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Synfacts 2010(7): 0803-0803
DOI: 10.1055/s-0029-1220084
DOI: 10.1055/s-0029-1220084
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Asymmetric Addition of 1,3-Diynes to Aldehydes
B. M. Trost*, V. S. Chan, D. Yamamoto
Stanford University, USA
Further Information
Publication History
Publication Date:
22 June 2010 (online)
Significance
Diyne carbinols are structural elements commonly found in fatty acid derived polyacetylenic natural products. The most common strategy in the preparation of these natural products relies on asymmetric reduction of an ynone followed by Cadiot-Chodkiewicz cross-coupling. The authors report on the ProPhenol-catalyzed asymmetric addition of 1,3-diynes to aldehydes. This strategy allows for the creation of stereochemistry and C-C bond formation to take place in one operation. This report represents the first efficient asymmetric addition of a 1,3-diyne to an aldehyde. The authors go on to demonstrate the power of this methodology in the synthesis of several natural products.