Brønsted Acid Catalyzed Asymmetric Propargylation of Aldehydes

Which gets activated? A versatile and highly enantioselective chiral Brønsted acid catalyzed method for the propargylation of aldehydes is described to provide a range of chiral homopropargylic alcohols. Computational studies support the belief that the chiral phosphoric acid activates the allenyl b...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2012-02, Vol.51 (6), p.1391-1394
Main Authors: Jain, Pankaj, Wang, Hao, Houk, Kendall N., Antilla, Jon C.
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Alkadienes - chemistry
Alkynes - chemical synthesis
Alkynes - chemistry
asymmetric catalysis
Boronic Acids - chemistry
Bromine Compounds - chemistry
Brønsted acid
Catalysis
homopropargylic alcohol
Models, Molecular
Propanols - chemistry
propargylation
Stereoisomerism
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Summary:Which gets activated? A versatile and highly enantioselective chiral Brønsted acid catalyzed method for the propargylation of aldehydes is described to provide a range of chiral homopropargylic alcohols. Computational studies support the belief that the chiral phosphoric acid activates the allenyl boronic acid pinacol ester reagent rather than the aldehyde.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201107407