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Asymmetric synthesis of gamma-hydroxy alpha,beta-unsaturated aldehydes via enantioselective direct addition of propargyl acetate to aldehydes

Asymmetric synthesis of gamma-hydroxy alpha,beta-unsaturated aldehydes via enantioselective direct addition of propargyl acetate to aldehydes

Organic Letters 3(19): 3017-3020

ISSN/ISBN: 1523-7060

PMID: 11554832

DOI: 10.1021/ol016431j

We report the first example of enantioselective and diastereoselective aldehyde additions of propargyl acetate to aldehydes using the methodology recently reported from our laboratories. Subsequent O-silyl protection, Pd-catalyzed isomerization, AcOH addition, and hydrolysis result in optically active gamma-hydroxy alpha,beta-unsaturated aldehydes as powerful building blocks. Reaction: see text.

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Accession: 045323639

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