Enantioselective Michael Addition/Iminium Ion Cyclization Cascades of Tryptamine-Derived Ureas

被引：36

作者：

Aillaud, Isabelle ^{[1
]}

Barber, David M. ^{[1
]}

Thompson, Amber L. ^{[1
]}

Dixon, Darren J. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Mansfield Rd, Oxford OX1 3TA, England

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 12期

基金：

英国工程与自然科学研究理事会;

关键词：

PICTET-SPENGLER REACTIONS; CHIRAL BRONSTED ACIDS; DIELS-ALDER REACTION; N-ACYLIMINIUM IONS; PHOSPHORIC-ACID; ABSOLUTE-STRUCTURE; INTERMOLECULAR ADDITION; CATALYSIS; INDOLES; ACCESS;

D O I：

10.1021/ol401039h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Michael addition/iminium ion cyclization cascade of enones with tryptamine-derived ureas under BINOL phosphoric acid (BPA) catalysis Is reported. The cascade reaction tolerates a wide variety of easily synthesized tryptamine-derived ureas, including those bearing substituents on the distal nitrogen atom of the urea moiety, affording polyheterocyclic products in good yields and good to excellent enantioselectivities.

引用

页码：2946 / 2949

页数：4

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