Stereoselective synthesis of γ-lactams from imines and cyanosuccinic anhydrides.
A reaction between imines and anhydrides has been developed with chiral disubstituted anhydrides and chiral imines. The synthesis of highly substituted γ-lactams with three stereogenic centers, including one quaternary center, proceeds at room temperature in high yield and with high diastereoselectivity in most cases. Enantiomerically pure alkyl-substituted anhydrides proceed with no epimerization, thus providing access to enantiomerically pure penta-substituted lactam products.
Department of Chemistry, University of California , Davis, One Shields Avenue, Davis, California 95616, United States, and Department of Chemistry, Oregon State University , 153 Gilbert Hall, Corvallis, Oregon 97331, United States.
Darlene Q
DQ
Tan
Ashkaan
A
Younai
Ommidala
O
Pattawong
James C
JC
Fettinger
Paul Ha-Yeon
PH
Cheong
Jared T
JT
Shaw
D007097:Imines / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013387:Succinic Anhydrides / Q000737:chemistry*
D007097:Imines; D007769:Lactams; D013387:Succinic Anhydrides