MECHANISM DRIVEN TRANS STEREOSPECIFICITY IN THE PICTET-SPENGLER REACTION - STEREOSPECIFIC FORMATION OF TRANS-1,2,3-TRISUBSTITUTED-TETRAHYDRO BETA-CARBOLINES BY CONDENSATION OF NB-DIPHENYLMETHYL TRYPTOPHAN ISOPROPYL ESTERS WITH ALDEHYDES

被引：32

作者：

CZERWINSKI, KM ^{[1
]}

DENG, L ^{[1
]}

COOK, JM ^{[1
]}

机构：

[1] UNIV WISCONSIN,DEPT CHEM,MILWAUKEE,WI 53201

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 33期

关键词：

D O I：

10.1016/S0040-4039(00)61268-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoelectronic control in the Pictet-Spengler condensation of N(b)-alkylsubstituted tryptophan alkyl esters has been employed to promote 100% stereoselectivity in this process. The reaction of N(b)-diphenylmethyl tryptophan isopropyl ester 8 with acetaldehyde in benzene at reflux yielded the trans-diastereomer 10d to the complete exclusion of the corresponding cis isomer. This trans stereospecificity was also observed for butyraldehyde and cyclohexylcarboxaldehyde.

引用

页码：4721 / 4724

页数：4

共 24 条

[1] BETA-CARBOLINES - SYNTHESIS AND NEUROCHEMICAL AND PHARMACOLOGICAL ACTIONS ON BRAIN BENZODIAZEPINE RECEPTORS [J].