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Asymmetric vinylogous aldol reaction of silyloxy furans with a chiral organic salt
Journal article   Open access

Asymmetric vinylogous aldol reaction of silyloxy furans with a chiral organic salt

Ravi P Singh, Bruce M Foxman and Li Deng
Journal of the American Chemical Society, Vol.132(28), pp.9558-9560
07/21/2010
PMCID: PMC2925177
PMID: 20583835

Abstract

Hydrogen Bonding Furans - chemistry Organic Chemicals - chemistry Aldol reactions Salts Aldehydes Stereoselectivity Catalysts
Despite their synthetic significance there is a general lack of asymmetric vinylogous aldol reactions that tolerate variations of both the silyloxy furans and aldehydes. We have developed a new chiral organic catalyst based on a carboxylate-ammonium salt prepared from a thiourea-amine and a carboxylic acid. This new catalyst enabled us to develop an efficient asymmetric vinylogous aldol reaction of unprecedented scope with respect to both 2-trimethylsilyloxy furans and aldehydes.
url
https://doi.org/10.1021/ja103331tView
Published (Version of record) Open

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