Asymmetric thio-Michael/nucleophilic addition domino reaction with chiral N-sulfinimines.
Optically active N-sulfinimines underwent stereoselective Michael/nucleophilic addition domino reaction triggered by magnesium thiolate to give alpha-phenylthiomethyl-beta-(N-sulfinylamino) esters in high diastereomeric excess. The adducts were readily converted into optically active alpha-methylene-beta-(N-sulfinylamino)esters so that this reaction provides a useful asymmetric aza-Baylis-Hillman-equivalent method.
Kamimura
Akio
A
Department of Applied Molecular Bioscience, Graduate School of Medicine, Yamaguchi University, Ube 755-8611, Japan. ak10@yamaguchi-u.ac.jp
Okawa
Hidenori
H
Morisaki
Yuki
Y
Ishikawa
Shingo
S
Uno
Hidemitsu
H
D002625:Chemistry, Organic / Q000379:methods*; D018360:Crystallography, X-Ray; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013441:Sulfinic Acids / Q000737:chemistry*; D013455:Sulfur; D047090:beta-Lactams / Q000737:chemistry
D007097:Imines; D013441:Sulfinic Acids; D047090:beta-Lactams; D013455:Sulfur