Copper Catalyzed Asymmetric Propargylation of Aldehydes

The highly enantio- and regioselective copper catalyzed asymmetric propargylation of aldehydes with a propargyl borolane reagent is reported. The methodology demonstrated broad functional group tolerance and provided high enantioselectivities for aliphatic, vinyl, and aryl aldehydes. The utility of...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2010-06, Vol.132 (22), p.7600-7601
Main Authors: Fandrick, Daniel R, Fandrick, Keith R, Reeves, Jonathan T, Tan, Zhulin, Tang, Wenjun, Capacci, Andrew G, Rodriguez, Sonia, Song, Jinhua J, Lee, Heewon, Yee, Nathan K, Senanayake, Chris H
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Boron Compounds - chemistry
Catalysis
Copper - chemistry
Molecular Structure
Stereoisomerism
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Summary:The highly enantio- and regioselective copper catalyzed asymmetric propargylation of aldehydes with a propargyl borolane reagent is reported. The methodology demonstrated broad functional group tolerance and provided high enantioselectivities for aliphatic, vinyl, and aryl aldehydes. The utility of the TMS homopropargylic alcohols was demonstrated by the facile conversion to a chiral dihydropyranone.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja103312x