Quinine-Catalysed Double Michael Addition of Malononitrile to 1,5-Disubstituted Pentadien-3-ones: A Stereoselective Route to Cyclohexanones

被引：24

作者：

De Fusco, Claudia ^{[1
]}

Lattanzi, Alessandra ^{[1
]}

机构：

[1] Univ Salerno, Dipartimento Chim & Biol, I-84084 Fisciano, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 20-21期

关键词：

Organocatalysis; Alkaloids; Michael addition; Cascade reactions; Diastereoselectivity; Enantioselectivity; ORGANOCATALYTIC CASCADE REACTIONS; DIPHENYLPROLINOL SILYL ETHER; ONE-POT; DIASTEREOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; STEREOCENTERS; SEQUENCE;

D O I：

10.1002/ejoc.201100282

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective synthesis of 4-oxo-2,6-diaryl-cyclohexane-1,1-dicarbonitriles has been developed through double Michael addition of malononitrile to 1,5-disubstituted pentadien-3-ones catalysed by quinine. This simple cascade pro-cess affords cyclohexanones in moderate-to-good yields, excellent diastereoselectivity and up to 86% ee. The isolation of the monoaddition product helps to shed light on the stereochemical outcome of the two-step process.

引用

页码：3728 / 3731

页数：4