Highly enantioselective Michael reactions catalyzed by a chiral quaternary ammonium salt. Illustration by asymmetric syntheses of (S)-ornithine and chiral 2-cyclohexenones.
[formula: see text] The use of the chiral quaternary ammonium salts 1a and 1b makes possible enantioselective Michael reactions which have been applied to the asymmetric syntheses of (S)-ornithine (2) and the chiral 2-cyclohexenone 6.
Zhang
F Y
FY
Department of Chemistry and Chemical Biology, Harvard University, Massachusetts 02138, USA.
Corey
E J
EJ
D002384:Catalysis; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009952:Ornithine / Q000138:chemical synthesis* / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D012492:Salts; D013057:Spectrum Analysis; D013237:Stereoisomerism
D003512:Cyclohexanones; D000644:Quaternary Ammonium Compounds; D012492:Salts; C028215:2-cyclohexen-1-one; D009952:Ornithine