title: N-triflylthiophosphoramide catalyzed enantioselective Mukaiyama aldol reaction of aldehydes with silyl enol ethers of ketones.
abstract: The first Brønsted acid catalyzed asymmetric Mukaiyama aldol reaction of aldehydes using silyl enol ethers of ketones as nucleophiles has been reported. A variety of aldehydes and silyl enol ethers of ketones afforded the aldol products in excellent yields and good to excellent enantioselectivities. Mechanistic studies revealed that the actual catalyst may be changed from the silylated Brønsted acid to the Brønsted acid itself depending on the reaction temperature.
authors.affiliation: Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60615, USA.
authors.forename: Cheol Hong
authors.initials: CH
authors.lastname: Cheon
authors.forename: Hisashi
authors.initials: H
authors.lastname: Yamamoto
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004987:Ethers / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009946:Organothiophosphorus Compounds / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D000447:Aldehydes; D004987:Ethers; D007659:Ketones; D009946:Organothiophosphorus Compounds; D012821:Silanes; C116609:3-hydroxybutanal
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