JPS5566522A - Preparation of optically active bicyclic compounds by asymmetric diels-alder reaction - Google Patents

Preparation of optically active bicyclic compounds by asymmetric diels-alder reaction

Info

Publication number
JPS5566522A
JPS5566522A JP13892978A JP13892978A JPS5566522A JP S5566522 A JPS5566522 A JP S5566522A JP 13892978 A JP13892978 A JP 13892978A JP 13892978 A JP13892978 A JP 13892978A JP S5566522 A JPS5566522 A JP S5566522A
Authority
JP
Japan
Prior art keywords
optically active
alder reaction
formula
diels
bicyclic compounds
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
Application number
JP13892978A
Other languages
Japanese (ja)
Other versions
JPS6239134B2 (en
Inventor
Kenji Koga
Shunichi Hashimoto
Nobuyasu Yoneshima
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nippon Chemiphar Co Ltd
Original Assignee
Nippon Chemiphar Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nippon Chemiphar Co Ltd filed Critical Nippon Chemiphar Co Ltd
Priority to JP13892978A priority Critical patent/JPS5566522A/en
Publication of JPS5566522A publication Critical patent/JPS5566522A/en
Publication of JPS6239134B2 publication Critical patent/JPS6239134B2/ja
Granted legal-status Critical Current

Links

Classifications

    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

PURPOSE: To obtain the title compound having pharmacological activity, in high optical purity and yield, by the Diels-Alder reaction of dienes and dienophiles using an optically active Lewis acid as an asymmetric catalyst.
CONSTITUTION: Optically active bicyclic compounds of formula IV (WX and WY denote that X and Y are in the absolute configuration) are obtained by [4+2] cyclization addition (Diels-Alder reaction) of dienes (e.g. cyclopentadiene of formula I) and dienophiles [e.g. α,β-unsaturated carbonyl compounds of formula II (X is alkoxycarbonyl, aldehyde or cyano; Y is H, halogen or alkyl), such as acrylic acid derivatives or acrolein derivatives, etc.] in the presence of an optically active Lewis acid [e.g. alkoxyalminum dichloride of formula III (R is an optically active alcohol residue), etc.] as an asymmetric catalyst. The presence of the asymmetric catalyst improves the purity and the yield of the product.
COPYRIGHT: (C)1980,JPO&Japio
JP13892978A 1978-11-13 1978-11-13 Preparation of optically active bicyclic compounds by asymmetric diels-alder reaction Granted JPS5566522A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP13892978A JPS5566522A (en) 1978-11-13 1978-11-13 Preparation of optically active bicyclic compounds by asymmetric diels-alder reaction

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP13892978A JPS5566522A (en) 1978-11-13 1978-11-13 Preparation of optically active bicyclic compounds by asymmetric diels-alder reaction

Publications (2)

Publication Number Publication Date
JPS5566522A true JPS5566522A (en) 1980-05-20
JPS6239134B2 JPS6239134B2 (en) 1987-08-21

Family

ID=15233431

Family Applications (1)

Application Number Title Priority Date Filing Date
JP13892978A Granted JPS5566522A (en) 1978-11-13 1978-11-13 Preparation of optically active bicyclic compounds by asymmetric diels-alder reaction

Country Status (1)

Country Link
JP (1) JPS5566522A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0641014A (en) * 1991-06-26 1994-02-15 Union Carbide Chem & Plast Technol Corp Manufacturing of unsaturated alicyclic ester and its derivative
JP2012087077A (en) * 2010-10-18 2012-05-10 Toyohashi Univ Of Technology Production method of optically active cyclohexene derivative, optically active cyclohexene derivative, and production method of optically active cyclohexadiene derivative and optically active cyclohexadiene derivative using the same

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0641014A (en) * 1991-06-26 1994-02-15 Union Carbide Chem & Plast Technol Corp Manufacturing of unsaturated alicyclic ester and its derivative
JP2012087077A (en) * 2010-10-18 2012-05-10 Toyohashi Univ Of Technology Production method of optically active cyclohexene derivative, optically active cyclohexene derivative, and production method of optically active cyclohexadiene derivative and optically active cyclohexadiene derivative using the same

Also Published As

Publication number Publication date
JPS6239134B2 (en) 1987-08-21

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