Enantioselective Synthesis of Janus Kinase Inhibitor INCB018424 via an Organocatalytic Aza-Michael Reaction

被引：129

作者：

Lin, Qiyan ^{[1
]}

Meloni, David ^{[1
]}

Pan, Yongchun ^{[1
]}

Xia, Michael ^{[1
]}

Rodgers, James ^{[1
]}

Shepard, Stacey ^{[1
]}

Li, Mei ^{[1
]}

Galya, Laurine ^{[1
]}

Metcalf, Brian ^{[1
]}

Yue, Tai-Yuen ^{[1
]}

Liu, Pingli ^{[1
]}

Zhou, Jiacheng ^{[1
]}

机构：

[1] Incyte Corp, Expt Stn, Wilmington, DE 19880 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 09期

关键词：

CATALYTIC CONJUGATE ADDITION; ALPHA; BETA-UNSATURATED KETONES; ASYMMETRIC-SYNTHESIS; CARBONYL-COMPOUNDS; N-HETEROCYCLES; ALDEHYDES; PEPTIDES; PATHWAY; DISEASE; IMIDES;

D O I：

10.1021/ol900350k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective synthesis of INCB018424 via organocatalytic asymmetric aza-Michael addition of pyrazoles (16 or 20) to (E)-3-cyclopentylacrylaldehyde (23) using diarylprolinol silyl ether as the catalyst was developed. Michael adducts (R)-24 and (R)-27 were isolated in good yield and high ee and were readily converted to INCB018424.

引用

页码：1999 / 2002

页数：4

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