Triple Role of Phenylselenonyl Group Enabled a One-Pot Synthesis of 1,3-Oxazinan-2-ones From α-Isocyanoacetates, Phenyl Vinyl Selenones, and Water

被引：68

作者：

Buyck, Thomas ^{[1
]}

Wang, Qian ^{[1
]}

Zhu, Jieping ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne, Lab Synth & Nat Prod, Inst Chem Sci & Engn, EPFL SB ISIC LSPN, CH-1015 Lausanne, Switzerland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 32期

基金：

瑞士国家科学基金会;

关键词：

ORGANOCATALYTIC MICHAEL ADDITION; FORMAL 3+2 CYCLOADDITION; ASYMMETRIC-SYNTHESIS; STEREOCONTROLLED SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; QUATERNARY STEREOCENTERS; MULTICOMPONENT SYNTHESIS; ARYL ISOCYANOESTERS; CATALYZED SYNTHESIS; N-SULFONYLIMINES;

D O I：

10.1021/ja506031h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reaction of alpha-substituted alpha-isocyanoacetates with phenyl vinyl selenones in the presence of a catalytic amount of base (DBU or Et3N, 0.05-0.1 equiv) followed by addition of p-toluenesulfonic acid (PTSA, 0.1-0.2 equiv) afforded 4,4,5-trisubstituted 1,3-oxazinan-2-ones in good to excellent yields. Enantiomerically enriched heterocycles can also be prepared using a Cinchona alkaloid-derived bifunctional organocatalyst for the Michael addition step. The phenylselenonyl group served as an activator for the Michael addition, a leaving group and a latent oxidant in this integrated reaction sequence.

引用

页码：11524 / 11528

页数：5

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