JPH02167254A - Production of optically active cyanohydrin or enantiomer thereof - Google Patents
Production of optically active cyanohydrin or enantiomer thereofInfo
- Publication number
- JPH02167254A JPH02167254A JP32299888A JP32299888A JPH02167254A JP H02167254 A JPH02167254 A JP H02167254A JP 32299888 A JP32299888 A JP 32299888A JP 32299888 A JP32299888 A JP 32299888A JP H02167254 A JPH02167254 A JP H02167254A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- group
- optically active
- enantiomer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000001207 fluorophenyl group Chemical group 0.000 claims abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 15
- 230000003287 optical effect Effects 0.000 abstract description 13
- -1 silane compound Chemical class 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 150000003609 titanium compounds Chemical class 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 3
- 239000000575 pesticide Substances 0.000 abstract 1
- 229910000077 silane Inorganic materials 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 description 11
- 239000002994 raw material Substances 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- CUJUQPVHWIDESZ-SNVBAGLBSA-N (2r)-2-hydroxy-4-phenylbutanenitrile Chemical compound N#C[C@H](O)CCC1=CC=CC=C1 CUJUQPVHWIDESZ-SNVBAGLBSA-N 0.000 description 2
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- LTEDQKPGOZDGRZ-UHFFFAOYSA-L propan-2-olate;titanium(4+);dichloride Chemical compound Cl[Ti+2]Cl.CC(C)[O-].CC(C)[O-] LTEDQKPGOZDGRZ-UHFFFAOYSA-L 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- BAFXROPRJIXZKC-UHFFFAOYSA-N 1,1,4,4-tetraphenylbutane-1,2,3,4-tetrol Chemical compound C=1C=CC=CC=1C(O)(C=1C=CC=CC=1)C(O)C(O)C(O)(C=1C=CC=CC=1)C1=CC=CC=C1 BAFXROPRJIXZKC-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- XPCFTKFZXHTYIP-PMACEKPBSA-N Benazepril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C2=CC=CC=C2CC1)=O)CC1=CC=CC=C1 XPCFTKFZXHTYIP-PMACEKPBSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940127088 antihypertensive drug Drugs 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- NDEIPVVSKGHSTL-UHFFFAOYSA-N butane-1,1,1,2-tetrol Chemical compound CCC(O)C(O)(O)O NDEIPVVSKGHSTL-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003899 tartaric acid esters Chemical class 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は光学活性シアノヒドリンの製造方法に関する。[Detailed description of the invention] [Industrial application field] The present invention relates to a method for producing optically active cyanohydrin.
光学活性シアノヒドリンは、医薬、農薬等の中間体とし
て重要な化合物である。例えば、（Ｒ）−１−シアノ−
３−フェニルプロパン−１−オールは、エナラプリン、
ベンザプリル、キナプレルなどに代表される血圧降下剤
の重要な中間体である。Optically active cyanohydrins are important compounds as intermediates for pharmaceuticals, agricultural chemicals, and the like. For example, (R)-1-cyano-
3-phenylpropan-1-ol is enalapurin,
It is an important intermediate for antihypertensive drugs such as benzapril and quinaprel.
従来アルデヒドを原料として光学活性シアノヒドリンを
合成する方法としては、光学活性ホウ素化合物を用いる
方法（Ｔｅｔｒａｈｅｄｒｏｎ Ｌｅｔｔ、＋ ２Ｌ
４７２Ｈ１９８６）） 、ｄ−オキシニトリラーゼを用
いる方法（Ａｎｇｅｗ、 Ｃｈｅｍ、、 ７７、１１３
９（１９６５） ） 、合成ペプチドを用いる方法（Ｂ
ｕｌｌ、 Ｃｈｅｍ、 Ｓｏｃ、 Ｊａｐａｎ、。Conventionally, as a method for synthesizing optically active cyanohydrin using aldehyde as a raw material, a method using an optically active boron compound (Tetrahedron Lett, + 2L
472H1986)), a method using d-oxynitrilase (Angew, Chem, 77, 113
9 (1965)), a method using synthetic peptides (B
ull, Chem, Soc, Japan.
５９、８９３（１９８６） ）などが知られているが、
得られたシアノヒドリンの光学純度は必ずしも満足でき
るものではない。また、本発明者らは、先に（２Ｒ、３
１１） −２，３−０−（１−フェニルエチリデン）−
１，１，４，４−テトラフェニル−１，２，３，４−ブ
タンテトロールと、ジクロロジイソプロポキシチタンと
から得られる光学活性チタン化合物を用いる方法を発明
し、特許出願を行った（特願昭６２〜２４８６３３号）
。しかしこの方法は、ベンズアルデヒドなどの芳香族ア
ルデヒドが原料の場合は、高い光学純度が得られるが、
３−フェニルプロパツール、ｎ−デカテールなどの脂肪
族アルデヒドが原料の場合は、必ずしも十分な光学純度
が得られないという欠点がある。59, 893 (1986)) are known, but
The optical purity of the obtained cyanohydrin is not necessarily satisfactory. In addition, the present inventors previously discovered (2R, 3
11) -2,3-0-(1-phenylethylidene)-
Invented a method using an optically active titanium compound obtained from 1,1,4,4-tetraphenyl-1,2,3,4-butanetetrol and dichlorodiisopropoxytitanium, and filed a patent application ( (Special Application No. 1986-248633)
. However, this method provides high optical purity when the raw material is an aromatic aldehyde such as benzaldehyde.
When aliphatic aldehydes such as 3-phenylpropatol and n-decater are used as raw materials, there is a drawback that sufficient optical purity cannot necessarily be obtained.
〔発明が解決しようとする課題〕
脂肪族アルデヒドを原料として、光学活性シアノヒドリ
ンを高い光学収率で合成する方法は知られておらず、光
学分割による方法に頼らざるを得ないのが現状である。[Problem to be solved by the invention] There is no known method for synthesizing optically active cyanohydrin with high optical yield using aliphatic aldehyde as a raw material, and currently we have no choice but to rely on a method using optical resolution. .
本発明は光学分割と言う操作を行うことなく高い光学純
度で脂肪族光学活性シアノヒドリンを合成する方法を提
供することを目的とするものである。An object of the present invention is to provide a method for synthesizing aliphatic optically active cyanohydrin with high optical purity without performing an operation called optical resolution.
本発明者らは、−紋穴
％式％（１）
（式中Ｒ１はアルキル基、アルケニル基、アラルキル基
またはシクロアルキル基を表わす。）で示される化合物
（以下化合物（１）と記す。）と−紋穴
％式％（）
（式中Ｒ２低級アルキル基を表わす。）で示される化合
物（以下化合物（ＩＩ）と記す。）とを−紋穴
％式％
（式中Ｒ３及びＲ４は同一または異なり、フェニル基ま
たは低級アルキル基を表わし、Ｒ５はフェニル基または
フルオロフェニル基ヲ表ワす。）
で示される光学活性チタン化合物（以下化合物（ＩＩＩ
）と記す。）またはその鏡像体の存在下に反応させるこ
とを特徴とする一般式
（式中Ｒ’は式（１）におけるのと同じ意味を表わす。The present inventors have developed a compound represented by the formula (1) (in which R1 represents an alkyl group, an alkenyl group, an aralkyl group, or a cycloalkyl group) (hereinafter referred to as compound (1)). and the compound represented by the formula (in the formula R2 represents a lower alkyl group) (hereinafter referred to as compound (II)) and the compound represented by the formula (in which R3 and R4 are the same) or differently, represents a phenyl group or a lower alkyl group, and R5 represents a phenyl group or a fluorophenyl group (hereinafter referred to as compound (III)).
). ) or its enantiomer (wherein R' represents the same meaning as in formula (1)).
）
で示される光学活性シアノヒドリン又はその鏡像体が好
収率かつ高い光学純度で得られることを見出し、本発明
に到達した。) It was discovered that the optically active cyanohydrin or its enantiomer represented by the following can be obtained in good yield and high optical purity, and the present invention was achieved.
前記の一般式中のＲ１、Ｒ２、Ｒ３、Ｒ４およびＲ５を
詳しく説明する。Ｒ１は前述のとおりアルキル基、アル
ケニル基、アラルキル基またはシクロアルキル基を表わ
す。ここでアルキル基としてはメチル基、エチル基、ｎ
−プロピル基、ｎ −ブチル基、ｎ−オクチル基などが
例示される。アルケニル基としてはアリル基、ブテニル
基、７オクテンー１−イル基、９−デセン−１−イル基
などが例示される。アラルキル基としてはフ玉ニルメチ
ル基、ｐ−ｔ−ブチルフェニルメチル基などが例示され
る。シクロアルキル基としてはシクロペンチル基、シク
ロヘキシル基などが例示される。Ｒ２は低級アルキル基
を表わすが、具体的にはメチル基、エチル基、プロピル
基が例示される。R1, R2, R3, R4 and R5 in the above general formula will be explained in detail. As mentioned above, R1 represents an alkyl group, an alkenyl group, an aralkyl group or a cycloalkyl group. Here, the alkyl group is a methyl group, an ethyl group, n
-propyl group, n-butyl group, n-octyl group, etc. are exemplified. Examples of the alkenyl group include an allyl group, a butenyl group, a 7-octen-1-yl group, and a 9-decen-1-yl group. Examples of the aralkyl group include a fluorinylmethyl group and a pt-butylphenylmethyl group. Examples of the cycloalkyl group include a cyclopentyl group and a cyclohexyl group. R2 represents a lower alkyl group, and specific examples include a methyl group, an ethyl group, and a propyl group.
Ｒ３およびＲ４は同一または異なり、フェニル基または
低級アルキル基を表わす。ここで低級アルキル基として
はメチル基、エチル基、プロピル基などが例示される。R3 and R4 are the same or different and represent a phenyl group or a lower alkyl group. Examples of lower alkyl groups include methyl, ethyl, and propyl groups.
Ｒ５はフェニル基またはフルオロフェニル基を表わす。R5 represents a phenyl group or a fluorophenyl group.
本発明で用いられる化合物（ＩＩ［）は例えば光学活性
な酒石酸エステルより下記の方法により製造することが
できる。Compound (II[) used in the present invention can be produced, for example, from an optically active tartaric acid ester by the following method.
Ｒ５Ｒ５
Ｒ５Ｒ５
本発明において化合物（ＩＩ［）を用いると化合物（Ｉ
Ｖ）が得られ、化合物（ＩＩ［）の鏡像体を用いると化
合物（ＩＶ）の鏡像体が得られる。R5R5 R5R5 When compound (II[) is used in the present invention, compound (I
V) is obtained, and when the enantiomer of compound (II[) is used, the enantiomer of compound (IV) is obtained.
本発明において使用する化合物（■）、化合物（ｎ）お
よび化合物（Ｉ［Ｉ）の使用比率は特に制限はないが、
高い光学収率を得るためには化合物（１）に対し化合物
（Ｉ［［）を当モルあるいはそれ以上用いることが好ま
しい。また化合物（ＩＩ）の使用量も化合物（Ｉ）に対
し当モルあるいはそれ以上用いることが好ましい。There is no particular restriction on the usage ratio of compound (■), compound (n) and compound (I [I) used in the present invention, but
In order to obtain a high optical yield, it is preferable to use equivalent mole or more of compound (I[[) to compound (1). Further, the amount of compound (II) to be used is preferably one molar or more relative to compound (I).
反応温度は通常−１００℃〜室温の範囲から選ばれるが
、高い光学純度を得るためには一１００℃〜−４０℃の
範囲内に設定するのが好ましい。The reaction temperature is usually selected from the range of -100°C to room temperature, but is preferably set within the range of -100°C to -40°C in order to obtain high optical purity.
本発明の反応は通常溶媒の存在下に行なわれる。The reaction of the present invention is usually carried out in the presence of a solvent.
用いられる溶媒は反応条件下゛において不活性な溶媒で
あれば特に制限はないが、本反応においてはジクロロメ
タンなどの塩素化炭化水素、トルエン、ヘンゼン、キシ
レン、ｎ−へキサン、シクロヘキサンなどの炭化水素溶
媒を用いることが好ましい。The solvent used is not particularly limited as long as it is inert under the reaction conditions, but in this reaction, chlorinated hydrocarbons such as dichloromethane, hydrocarbons such as toluene, Hensen, xylene, n-hexane, and cyclohexane are used. Preferably, a solvent is used.
以下に本発明の実施例を示し、更に詳しく説明する。Examples of the present invention will be shown below and explained in more detail.
実施例１
（化合物（ｌｌｌａ）の合成）
（２１？ 、 ３Ｒ）−２，３−〇−（１−フェニルエ
チリデン）−１，１，４，４−テトラフェニル−１，２
，３，４ブタンテトラオール（２９１ｍｇ、 ０．５５
ｍｍｏｆ）のトルーエン溶ン＆（ｌｎｖ）をジクロ
ロジイソプロポキシチタン（１１９ｍｇ、 ０．５ ｍ
ｍｏ６）のトルエン溶液（１ｍｌ）に加え、室温にて１
時間攪拌した後、シアノトリメチルシラン（２５０ｍｇ
、 ２．５ｍｍｏ ｌ ）のトルエン溶液（１ｍｊ２）
に加え、室温にて１時間撹拌した。この液のプロトンＮ
ＭＲの分析により、クロロトリメチルシランと下記の化
合物（Ｉ［Ｉａ）の生成が認められた。Example 1 (Synthesis of compound (llla)) (21?, 3R)-2,3-〇-(1-phenylethylidene)-1,1,4,4-tetraphenyl-1,2
, 3,4 butanetetraol (291 mg, 0.55
mmof) in toluene & (lnv) in dichlorodiisopropoxytitanium (119 mg, 0.5 m
Add to a toluene solution (1 ml) of mo6) and add 1 mL at room temperature.
After stirring for an hour, cyanotrimethylsilane (250 mg
, 2.5 mmol) in toluene solution (1 mj2)
and stirred at room temperature for 1 hour. Proton N of this liquid
MR analysis confirmed the formation of chlorotrimethylsilane and the following compound (I[Ia).
（光学活性シアノヒドリンの合成）
前記の化合物（Ｉｌｌａ）の溶液を一７８°Ｃに冷却し
、３−フェニルプロパナール（６７ｍｇ、 ０．５ ｍ
ｍｏｆ）を加え、同温度で２４時間反応させた。反応終
了後、ｐＨ７のリン酸緩衝液にてクエンチし、セライト
を濾過助剤として濾過した。酢酸エチルを用いて有機物
を抽出した後、硫酸ナトリウムにより乾燥し、分取用の
１層クロマトグラフィーにより精製し、（２Ｒ）−ヒド
ロキシ−４−フェニルブタンニトリル（７１ｍｇＸｏ、
４４ ｍｍｏｌ を得た。収−ぢ８８％、〔α）”−
６，７９’ （ｃ＝２．０４、ＣＨＣｌ３）、光学純
度９１％。(Synthesis of optically active cyanohydrin) A solution of the above compound (Illa) was cooled to -78°C, and 3-phenylpropanal (67 mg, 0.5 m
mof) was added and reacted at the same temperature for 24 hours. After the reaction was completed, it was quenched with a pH 7 phosphate buffer and filtered using Celite as a filter aid. After extracting the organic matter using ethyl acetate, it was dried with sodium sulfate and purified by preparative single-layer chromatography to obtain (2R)-hydroxy-4-phenylbutanenitrile (71 mgXo,
44 mmol was obtained. Yield: 88%, [α)”-
6,79' (c=2.04, CHCl3), optical purity 91%.
実施例２〜５
実施例１と同様にして化合物（Ｉ［Ｉ ａ ）の溶液を
調製し、表１に示すアルデヒドを原料として、実施例１
と同様の操作により、光学活性シアノヒドリンの台底を
おこなった。結果を表１に示す。Examples 2 to 5 A solution of compound (I [I a ) was prepared in the same manner as in Example 1, and using the aldehyde shown in Table 1 as a raw material, Example 1
The bottom of the optically active cyanohydrin was prepared using the same procedure as above. The results are shown in Table 1.
以下余白
〔発明の効果〕
本発明によれば、農薬、医薬等の中間体として重要な光
学活性シアノヒドリンまたはその鏡像体を好収率かつ高
い光学純度で製造することができる。Margins below [Effects of the Invention] According to the present invention, optically active cyanohydrin or its enantiomer, which is important as an intermediate for agricultural chemicals, medicines, etc., can be produced in good yield and with high optical purity.
特許出願人 株式会社 り ラPatent applicant: Rilla Co., Ltd.
Claims (1)
基またはシクロアルキル基を表わす。）で示される化合
物と一般式 Ｒ＾２＿３ＳｉＣＮ（II） （式中Ｒ＾２低級アルキル基を表わす。） で示される化合物とを一般式 ▲数式、化学式、表等があります▼（III） （式中Ｒ＾３及びＲ＾４は同一または異なり、フェニル
基または低級アルキル基を表わし、Ｒ＾５はフェニル基
またはフルオロフェニル基を表わす。） で示される光学活性チタン化合物またはその鏡像体の存
在下に反応させることを特徴とする一般式▲数式、化学
式、表等があります▼ （式中Ｒ＾１は式（ I ）におけるのと同じ意味を表わ
す。） で示される光学活性シアノヒドリンまたはその鏡像体の
製造方法。[Claims] A compound represented by the general formula R^1CHO(I) (wherein R^1 represents an alkyl group, an alkenyl group, an aralkyl group, or a cycloalkyl group) and a general formula R^2_3SiCN(II) (In the formula, R^2 represents a lower alkyl group.) The compound represented by the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (III) (In the formula, R^3 and R^4 are the same or different, phenyl or a lower alkyl group, and R^5 represents a phenyl group or a fluorophenyl group.) General formula ▲Mathematical formula, chemical formula , tables, etc.▼ (In the formula, R^1 represents the same meaning as in formula (I).) A method for producing an optically active cyanohydrin or its enantiomer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32299888A JPH02167254A (en) | 1988-12-20 | 1988-12-20 | Production of optically active cyanohydrin or enantiomer thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32299888A JPH02167254A (en) | 1988-12-20 | 1988-12-20 | Production of optically active cyanohydrin or enantiomer thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02167254A true JPH02167254A (en) | 1990-06-27 |
| JPH0584304B2 JPH0584304B2 (en) | 1993-12-01 |
Family
ID=18149996
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP32299888A Granted JPH02167254A (en) | 1988-12-20 | 1988-12-20 | Production of optically active cyanohydrin or enantiomer thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02167254A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0683003U (en) * | 1993-05-20 | 1994-11-29 | 林電気株式会社 | Ultrasonic probe |
-
1988
- 1988-12-20 JP JP32299888A patent/JPH02167254A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0584304B2 (en) | 1993-12-01 |
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