An Enantioselective Synthesis of an 11-β-HSD‑1 Inhibitor via an Asymmetric Methallylation Catalyzed by (S)‑3,3′‑F2‑BINOL

An efficient asymmetric synthesis of 11-β-HSD inhibitor 1 has been accomplished in five linear steps and 53% overall yield, starting from the readily available 3-chloro-1-phenylpropan-1-one. The key feature of the synthesis includes an asymmetric methallylation of 3-chloro-1-phenylpropan-1-one catal...

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Bibliographic Details
Published in:Journal of organic chemistry 2016-03, Vol.81 (6), p.2665-2669
Main Authors: Zhang, Yongda, Wu, Jiang-Ping, Li, Guisheng, Fandrick, Keith R, Gao, Joe, Tan, Zhulin, Johnson, Joe, Li, Wenjie, Sanyal, Sanjit, Wang, Jun, Sun, Xiufeng, Lorenz, Jon C, Rodriguez, Sonia, Reeves, Jonathan T, Grinberg, Nelu, Lee, Heewon, Yee, Nathan, Lu, Bruce Z, Senanayake, Chris H
Format: Article
Language:English
Subjects:
11-beta-Hydroxysteroid Dehydrogenases - antagonists & inhibitors
11-beta-Hydroxysteroid Dehydrogenases - chemistry
Catalysis
Ketones - chemistry
Naphthols - chemical synthesis
Naphthols - chemistry
Propane - analogs & derivatives
Propane - chemical synthesis
Propane - chemistry
Stereoisomerism
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Summary:An efficient asymmetric synthesis of 11-β-HSD inhibitor 1 has been accomplished in five linear steps and 53% overall yield, starting from the readily available 3-chloro-1-phenylpropan-1-one. The key feature of the synthesis includes an asymmetric methallylation of 3-chloro-1-phenylpropan-1-one catalyzed by the highly effective organocatalyst (S)-3,3′-F2-BINOL under solvent-free and metal-free conditions.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b00189