Title:
ASYMMETRIC DIELS-ALDER REACTION
Document Type and Number:
Japanese Patent JP3915127
Kind Code:
B2
Abstract:
PROBLEM TO BE SOLVED: To readily obtain an optically active Diels-Alder adduct useful as a medicinal intermediate, etc., according to a new method for using a specific optically active complex and an oxidizing agent in combination as a Lewis acid catalyst and reacting a diene compound with a dienophilic compound.
SOLUTION: An optically active manganese complex compound of formula I (R1 to R4 are each H, a 1-4C alkyl, etc.; Y1 to Y4 are each H, phenyl, etc.; X is an anion pair capable of forming a salt) and an oxidizing agent (e.g. diiodobenzene) are used as a catalyst to carry out the Diels-Alder reaction of a diene compound of formula II (Z1 to Z6 are each H, a halogen, etc.) (e.g. cyclopentadiene) with a dienophilic compound of formula III (W1 to W4 are each H, formyl, etc.) (e.g. α-bromoacrolein) to afford the objective compound of formula IV (the absolute configurations of C atoms marked with * are R or S). The compound of formula II is preferably used in a molar amount of 1-5 times based on the compound of formula III and the complex of formula I is usually used in an amount of 0.1-5mol% based on the compound of formula III.
Inventors:
Katsuki Tsutomu
Application Number:
JP22508695A
Publication Date:
May 16, 2007
Filing Date:
September 01, 1995
Export Citation:
Assignee:
Nissan Chemical Industry Co., Ltd.
International Classes:
B01J31/16; C07B37/12; C07B33/00; C07B53/00; C07B61/00; C07C2/52; C07C13/20; C07C13/42; C07C17/30; C07C23/30; C07C41/30; C07C43/188; C07C45/69; C07C47/42; C07C49/543; C07C67/347; C07C69/75; C07C69/757; C07C253/30; C07C255/46; C07F13/00; (IPC1-7): C07B37/12; B01J31/16; C07B33/00; C07B53/00; C07C2/52; C07C13/20; C07C13/42; C07C17/30; C07C23/30; C07C41/30; C07C43/188; C07C45/69; C07C47/42; C07C49/543; C07C67/347; C07C69/75; C07C69/757; C07C253/30; C07C255/46; C07F13/00; //C07B61/00; C07M7:00
Domestic Patent References:
| JP7188092A | ||||
| JP55066522A | ||||
| JP6080656A | ||||
| JP63063789A | ||||
| JP5301878A |
Other References:
YAMASHITA Y. and KATSUKI T.,Synlett,1995年,p.829-830