N-triflylthiophosphoramide catalyzed enantioselective Mukaiyama aldol reaction of aldehydes with silyl enol ethers of ketones.
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.
Cheon
Cheol Hong
CH
Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60615, USA.
Yamamoto
Hisashi
H
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
D000447:Aldehydes; D004987:Ethers; D007659:Ketones; D009946:Organothiophosphorus Compounds; D012821:Silanes; C116609:3-hydroxybutanal
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