Asymmetric bronsted acid catalysis: Enantioselective nucleophilic substitutions and 1,4-additions

被引：318

作者：

Rueping, Magnus ^{[1
]}

Nachtsheim, Boris J. ^{[1
]}

Moreth, Stefan A. ^{[1
]}

Bolte, Michael ^{[1
,2
]}

机构：

[1] Goethe Univ Frankfurt, Inst Org Chem & Chem Biol, D-60438 Frankfurt, Germany

[2] Goethe Univ Frankfurt, Inst Inorgan & Analyt Chem, D-60439 Frankfurt, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 03期

关键词：

alkylation; atropisomers; Michael addition; nucleophilic substitution; organocatalysis;

D O I：

10.1002/anie.200703668

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Executive decision: Depending on the catalyst (both N-triflylphosphoramides), the highly enantioselective Brønsted acid catalyzed addition of indoles to α,β-unsaturated carbonyl compounds provides either α-keto esters (up to 92% ee, left side of the scheme), or a novel type of bisindole (right), which displays atropisomerism. The α-keto esters can also be converted into amino acids by a one-pot 1,4-addition-reductive amination reaction. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：593 / 596

页数：4

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