Issue 16, 2018

C6′ steric bulk of cinchona alkaloid enables an enantioselective Michael addition/annulation sequence toward pyranopyrazoles

Abstract

A catalytic asymmetric Michael addition/annulation process between pyrazolones and enynones towards enantioenriched pyranopyrazoles was developed. Key features include the development of a cinchona alkaloid with C6′ steric bulk as a competent catalyst and the observation of a unique stereospecific deuteration α to the keto group via a conducted tour pathway.

Graphical abstract: C6′ steric bulk of cinchona alkaloid enables an enantioselective Michael addition/annulation sequence toward pyranopyrazoles

Supplementary files

Article information

Article type
Communication
Submitted
08 Jan 2018
Accepted
29 Jan 2018
First published
29 Jan 2018

Chem. Commun., 2018,54, 2028-2031

C6′ steric bulk of cinchona alkaloid enables an enantioselective Michael addition/annulation sequence toward pyranopyrazoles

X. Bao, S. Wei, J. Qu and B. Wang, Chem. Commun., 2018, 54, 2028 DOI: 10.1039/C8CC00154E

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