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J Am Chem Soc. 2012 Apr 25;134(16):6924-7. doi: 10.1021/ja301196x. Epub 2012 Apr 17.

Enantioselective synthesis of dihydropyrazoles by formal [4+1] cycloaddition of in situ-derived azoalkenes and sulfur ylides.

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1
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, China.

Abstract

An unprecedented strategy to access highly enantioenriched dihydropyrazoles is described. It involves formal [4+1] cycloadditions of in situ-derived azoalkenes and sulfur ylides catalyzed by a chiral copper/Tol-BINAP complex. A variety of synthetically and biologically important dihydropyrazoles have been obtained with high enantioselectivities (up to 97:3 er) in good yields (83-97%).

PMID:
22497267
DOI:
10.1021/ja301196x
[Indexed for MEDLINE]

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