Enantioselective BINOL-phosphoric acid catalyzed Pictet-Spengler reactions of N-benzyltryptamine

被引：130

作者：

Sewgobind, Nishant V. ^{[1
]}

Wanner, Martin J. ^{[1
]}

Ingemann, Steen ^{[1
]}

de Gelder, Rene ^{[1
]}

van Maarseveen, Jan H. ^{[1
]}

Hiemstra, Henk ^{[1
]}

机构：

[1] Univ Amsterdam, Vant Hoff Inst Mol Sci, NL-1018 WS Amsterdam, Netherlands

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 16期

关键词：

D O I：

10.1021/jo8010478

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Optically active tetrahydro-beta-carbolines were synthesized via an (R)-BINOL-phosphoric acid-catalyzed asynunetric Pictet-Spengler reaction of N-benzyltryptamine with a series of aromatic and aliphatic aldehydes. The tetrahydro-beta-carbolines were obtained in yields ranging from 77% to 97% and with ee values up to 87%. The triphenylsilyl-substituted BINOL-phosphoric acid proved to be the catalyst of choice for the reaction with aromatic aldehydes. For the aliphatic aldehydes, 3,5 -bistrifluoromethylphenyL-substituted BINOL-phosphoric acid was identified as the best catalyst.

引用

页码：6405 / 6408

页数：4

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