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

Autor:	Nelu Grinberg, Jun Wang, Guisheng Li, Jon C. Lorenz, Joe Johnson, Xiufeng Sun, Heewon Lee, Yongda Zhang, Wenjie Li, Joe Gao, Sanjit Sanyal, Zhulin Tan, Nathan K. Yee, Bruce Z. Lu, Keith R. Fandrick, Jiang-Ping Wu, Chris H. Senanayake, Jonathan T. Reeves, Sonia Rodriguez
Rok vydání:	2016
Předmět:	010405 organic chemistry Chemistry Stereochemistry Organic Chemistry Enantioselective synthesis Stereoisomerism Naphthols Ketones 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Propane Yield (chemistry) 11-beta-Hydroxysteroid Dehydrogenases
Zdroj:	The Journal of Organic Chemistry. 81:2665-2669
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.6b00189
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::c05ceb16ed339e16e6c600f05b32d8f7 https://doi.org/10.1021/acs.joc.6b00189 Zobrazit plný text záznamu