Abstract
We report in this paper a flexible approach to (4S,5S)-5-alkyl-1-benzyl-4-benzyloxy-2-pyrrolidinones 7 starting from the known 5-alkyl-1-benzyl-4-benzyloxy-5-hydroxy-2-pyrrolidinones 6 . The method is based on TMSCl-mediated reductive dehydroxylation of 6 with Zn(BH4)2, which allows the synthesis of a variety of 2-pyrrolidinones 7 in 48-75% yields with cis/trans diastereoselectivities ranging from 58:42 to 90:10.
ACKNOWLEDGMENTS
The authors are grateful to the National Science Foundation (NSF) of China (Grant No. 20772099) and National Fund for Fostering Talents of Basic Science (NFFTBS) (No. J0630429) for financial support.
Notes
a Isolated yield.
b Ratio determined by column chromatographyic separation.
c Determined by 1H NMR analysis.