Asymmetric Mukaiyama aldol reaction of nonactivated ketones catalyzed by allo-threonine-derived oxazaborolidinone.
Asymmetric Mukaiyama aldol reaction of nonactivated ketones is realized for the first time by using an oxazaborolidinone catalyst derived from O-benzoyl-N-tosyl-allo-threonine. By employing a dimethylsilyl ketene S,O-acetal as a nucleophile, a variety of acetophenone derivatives afford the corresponding tertiary beta-hydroxy carbonyl compounds with high enantioselectivity up to 98% ee.
Adachi
Shinya
S
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan.
Harada
Toshiro
T
D000447:Aldehydes / Q000737:chemistry*; D001880:Boranes; D002384:Catalysis; D005030:Ethylenes / Q000737:chemistry*; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013912:Threonine / Q000737:chemistry
D000447:Aldehydes; D001880:Boranes; D005030:Ethylenes; D006573:Heterocyclic Compounds, 1-Ring; D007659:Ketones; C527334:oxazaborolidinone; D013912:Threonine; C116609:3-hydroxybutanal; C008223:ketene