Asymmetric vinylogous aldol reaction of silyloxy furans with a chiral organic salt.
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.
Singh
Ravi P
RP
Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Foxman
Bruce M
BM
Deng
Li
L
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000737:chemistry*; D006860:Hydrogen Bonding; D009930:Organic Chemicals / Q000737:chemistry*; D012492:Salts / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D005663:Furans; D009930:Organic Chemicals; D012492:Salts; C116609:3-hydroxybutanal