Organocatalytic Michael Reaction of Nitroenamine Derivatives with Aldehydes: Short and Efficient Asymmetric Synthesis of (-)-Oseltamivir

被引：35

作者：

Weng, Jiang ^{[1
]}

Li, Yong-Bo ^{[1
]}

Wang, Rui-Bin ^{[1
]}

Lu, Gui ^{[1
,2
]}

机构：

[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Inst Drug Synth & Pharmaceut Proc, Guangzhou 510006, Guangdong, Peoples R China

[2] Sun Yat Sen Univ, Inst Human Virol, Guangzhou 510080, Guangdong, Peoples R China

来源：

CHEMCATCHEM | 2012年 / 4卷 / 07期

关键词：

asymmetric synthesis; Michael addition; nitroenamines; organocatalysis; oseltamivir; OSELTAMIVIR PHOSPHATE TAMIFLU; ADDITION-ELIMINATION PROCESS; AZIDE-FREE SYNTHESIS; CONJUGATE ADDITION; NEURAMINIDASE INHIBITORS; CHEMOENZYMATIC SYNTHESIS; CONCISE SYNTHESIS; VINYL SULFONES; INFLUENZA; KETONES;

D O I：

10.1002/cctc.201200124

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Nitroenamine derivatives were used as a new class of Michael acceptors in the organocatalytic Michael reaction of aldehydes. The addition products were obtained in good yields and very good to excellent enantioselectivities. Moreover, a highly efficient, enantioselective, and simple synthesis of (-)-oseltamivir was accomplished in only five steps: two separate one-pot operations and one purification step. This procedural simplicity demonstrated the power of the organocatalytic asymmetric Michael reaction of nitroenamine acceptors with aldehydes.

引用

页码：1007 / 1012

页数：6

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