A Concise Enantioselective Synthesis of ( S )-Preclamol via Asymmetric Catalytic Negishi Cross-Coupling Reaction

被引：8

作者：

Zhou, Yun ^{[1
]}

Liu, Chunxiao ^{[1
]}

Wang, Lifeng ^{[1
]}

Han, Leng ^{[1
]}

Hou, Shicong ^{[1
]}

Bian, Qinghua ^{[1
]}

Zhong, Jiangchun ^{[1
]}

机构：

[1] China Agr Univ, Dept Appl Chem, 2 West Yuanmingyuan Rd, Beijing 100193, Peoples R China

来源：

SYNLETT | 2019年 / 30卷 / 07期

关键词：

(S)-peclamol; enantioselective Negishi cross-coupling; cobalt; asymmetric synthesis; chiral drug; AGONIST (-)-3-(3-HYDROXYPHENYL)-N-N-PROPYLPIPERIDINE PRECLAMOL; DOPAMINE-D-2; RECEPTOR; ALKYL ELECTROPHILES; 3-PPP; SELECTIVITY; RESOLUTION; (-)-3-PPP;

D O I：

10.1055/s-0037-1611759

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel, concise, and efficient enantioselective synthesis of ( S )-preclamol (87% ee, 51% total yield) has been developed. The key steps of this synthetic approach included cobalt-catalyzed asymmetric catalytic cross-coupling of -bromo ester with arylzinc and the reduction of chiral ester to diol with a tertiary carbon atom. Moreover, it was demonstrated that our enantioselective Negishi cross-coupling was a powerful tool to construct stereogenic benzylmethyl center in chiral drugs on a gram scale.

引用

页码：860 / 862

页数：3

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