A SUCCESSFUL ACID-PROMOTED ASYMMETRIC PICTET-SPENGLER REACTION OF N-A-BOC PROTECTED TRYPTOPHANS - EFFECT OF THE BOC GROUP ON REACTIVITY AND STEREOSELECTIVITY

被引：10

作者：

ZHANG, PW ^{[1
]}

COOK, JM ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 39期

关键词：

D O I：

10.1016/0040-4039(95)01448-Q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-a-BOC protected tryptophans 1 and 2 successfully undergo the Pictet-Spengler cyclization with a series of aldehydes in the presence of an acid catalyst (p-TSA) to furnish a mixture of trans and cis 1,2,3,4-tetrahydro-beta-carbolines (3 and 4). During removal of the BOC function with TFA, the mixture of trans (3) and cis (4) isomers was enantiospecifically converted into the trans N-a-H 1,2,3,4-tetrahydro-beta-carboline 5, a key intermediate for the construction of N-a-H substituted sarpagine alkaloids.

引用

页码：6999 / 7002

页数：4