Issue 6, 2015

CuBr2-catalyzed enantioselective routes to highly functionalized and naturally occurring allenes

Abstract

Here we show the CuBr2-catalyzed approach for highly enantioselective synthesis (90–98% ee) of allenes bearing a very broad array of unmasked synthetically attractive functionalities from aldehydes and terminal alkynyl bearing reactive functionalities with the absolute configuration controlled by applying readily available (R)- or (S)-α,α-diphenylprolinol. Following this protocol, the highly enantioselective synthesis of some naturally occurring allenes loaded with reactive functionalities becomes simple: a terminal alkyne plus an aldehyde. In comparison, they were reported to be synthesized either from similar level generic chemicals with much more steps or in lower ees.

Graphical abstract: CuBr2-catalyzed enantioselective routes to highly functionalized and naturally occurring allenes

Supplementary files

Article information

Article type
Research Article
Submitted
12 Mar 2015
Accepted
07 Apr 2015
First published
09 Apr 2015

Org. Chem. Front., 2015,2, 688-691

CuBr2-catalyzed enantioselective routes to highly functionalized and naturally occurring allenes

X. Tang, X. Huang, T. Cao, Y. Han, X. Jiang, W. Lin, Y. Tang, J. Zhang, Q. Yu, C. Fu and S. Ma, Org. Chem. Front., 2015, 2, 688 DOI: 10.1039/C5QO00084J

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