On the reaction of tryptophan derivatives with N-phenylselenyl phthalimide:: The nature of the kinetic and thermodynamic hexahydropyrrolo[2,3-b]indole products.: Alkylation of tryptophan with inversion of configuration

被引：50

作者：

Crich, D ^{[1
]}

Huang, XH ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 19期

关键词：

D O I：

10.1021/jo991093+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cyclization of a range of tryptophan derivatives with N-phenylselenyl phthalimide leading to 3a-phenylselenyl-1,2,3,3a,8,8a-hexahydro[2,3b]pyrroloindoles has been studied. It is established that in each case the kinetic diastereomer has the C-2 substituent on the exo face of the diazabicyclo[3.3.0]octane skeleton, whereas the thermodynamic isomers have the C-2 substituent endo. A simple protocol for the alkylation of tryptophan, leading to alpha-substituted tryptophans with clean inversion of configuration, is presented.

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页码：7218 / 7223

页数：6

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