Asymmetric vinylogous aldol reaction of silyloxy furans with a chiral organic salt
- PMID: 20583835
- PMCID: PMC2925177
- DOI: 10.1021/ja103331t
Asymmetric vinylogous aldol reaction of silyloxy furans with a chiral organic salt
Abstract
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.
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