JP7220466B2 - 光学活性ベンズアザボロール誘導体およびその製造方法 - Google Patents
光学活性ベンズアザボロール誘導体およびその製造方法 Download PDFInfo
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(A)の機器データ:
1H NMR (400 MHz, CD3OD): δ 8.94 (d, J = 4.5 Hz, 1H), 8.44 (d, J = 7.7 Hz, 1H), 8.10 (d, J = 8.4 Hz, 1H), 7.86-7.71 (m, 3H), 7.49 (d, J = 6.6 Hz, 1H), 7.20-6.96 (m, 2H), 6.86 (br s, 1H), 6.00-5.76 (m, 1H), 5.27-4.95 (m, 3H), 3.88 (br, 2H), 3.59-3.21 (m, 3H), 3.05-2.67 (m, 2H), 2.36 (br s, 1H), 1.62 (br s, 3H), 1.40-1.28 (m, 1H), 0.73 (br s, 1H); 13C NMR (100 MHz, CD3OD): δ 150.8, 149.1, 144.9, 142.6, 134.1, 131.2, 130.2, 129.6, 128.6, 128.3, 127.9, 124.8, 121.6, 115.0, 61.3, 56.6, 52.2, 41.9, 40.8, 28.7, 28.4, 26.6; IR (neat) 3255, 3060, 3001, 2941, 1593, 1446, 1392, 1360, 1218, 745 cm-1; HRMS (ESI+) calcd for C26H29BN3O [M + H]+ 410.2404: found 410.2394; [α]D 24 = +36.8 (c = 1.0, CHCl3).
次に、この得られた光学活性ベンズアザボロール誘導体(4)8.2mgを触媒として活用し、cis-1,2-シクロヘキサンジオールと塩化スルホニルの不斉スルホニル化反応を行った。その結果を下記反応式(6)に示しておく。
Claims (2)
- 下記式(2)で示されるシンコナアルカロイドの水酸基をアミノ基に変換したシンコナアルカロイド誘導体と2-ホルミルフェニルボロン酸との還元的アルキル化の後、分子内脱水反応によって下記式(1)で示される光学活性ベンズアザボロール誘導体を製造する方法。
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2008163022A (ja) | 2006-12-20 | 2008-07-17 | Brandeis Univ | シンコナアルカロイド触媒不斉マンニッヒ反応 |
JP2015145344A (ja) | 2014-02-03 | 2015-08-13 | 国立大学法人 名古屋工業大学 | 光学活性な四置換不斉炭素を有するα,β−ジアミノ酸類の製造方法 |
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EP3168208A1 (en) * | 2015-11-11 | 2017-05-17 | Quimica Sintetica, S.A. | Processes for the preparation of diastereomerically and enantiomerically enriched oxazolines |
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Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2008163022A (ja) | 2006-12-20 | 2008-07-17 | Brandeis Univ | シンコナアルカロイド触媒不斉マンニッヒ反応 |
JP2015145344A (ja) | 2014-02-03 | 2015-08-13 | 国立大学法人 名古屋工業大学 | 光学活性な四置換不斉炭素を有するα,β−ジアミノ酸類の製造方法 |
Non-Patent Citations (4)
Title |
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Farooq, Umar, et al.,Synthesis of new enantiomerically pure organoiodine catalysts and their application in the α-functi,Synthesis,2010年,6,1023-1029 |
Girija S Singh,Recent applications of Cinchona alkaloid-based catalysts in asymmetric addition reactions,Reports in Organic Chemistry,2016年,6,p.47-75 |
Rana, Nirmal K., et al.,Highly Enantioselective Organocatalytic Sulfa-Michael Addition to α,β-Unsaturated Ketones,Journal of Organic Chemistry,2010年,75(6),2089-2091 |
小林 雄一,シンコナアルカロイドの合成,有機合成化学協会誌,2007年,Vol.65 No.6,p.598-607 |
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