One-Pot Synthesis of (S)-Baclofen via Aldol Condensation of Acetaldehyde with Diphenylprolinol Silyl Ether Mediated Asymmetric Michael Reaction as a Key Step

被引：40

作者：

Hayashi, Yujiro ^{[1
]}

Sakamoto, Daisuke ^{[1
]}

Okamura, Daichi ^{[1
]}

机构：

[1] Tohoku Univ, Dept Chem, Grad Sch Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 01期

关键词：

HIGH-YIELDING SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; INHIBITOR (-)-OSELTAMIVIR; ALLYLIC ALKYLATION; ALDEHYDES; NITROMETHANE; BACLOFEN; NITROALKANES; NITROOLEFINS; HOMOLOGATION;

D O I：

10.1021/acs.orglett.5b02839

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient asymmetric total synthesis of (S)-baclofen was accomplished via a one-pot operation from commercially available materials using sequential reactions, such as aldol condensation of acetaldehyde, diphenylprolinol silyl ether mediated asymmetric Michael reaction of nitromethane, Kraus-Pinnick oxidation, and Raney Ni reduction. Highly enantioenriched baclofen was obtained in one pot with a good yield over four reactions.

引用

页码：4 / 7

页数：4

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