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
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
收藏
页码:1007 / 1012
页数:6
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