A Stereoselective Cyclization Strategy for the Preparation of gamma-Lactams and Their Use in the Synthesis of alpha-Methyl-beta-Proline

作者：Banerjee Souvik; Smith Justin; Smith Jillian; Faulkner Caleb; Masterson Douglas S^*

来源：Journal of Organic Chemistry, 2012, 77(23): 10925-10930.

DOI：10.1021/jo3015903

A straightforward stereoselective and enantiodivergent cyclization strategy for the construction of gamma-lactams is described. The cyclization strategy makes use of chiral malonic esters prepared from enantiomerically enriched monoesters of disubstituted malonic acid. The cyclization occurs with the selective displacement of a substituted benzyl alcohol as the leaving group. A Hammett study illustrates that the cyclization is under electronic control. The resulting gamma-lactam can be readily converted into a novel proline analogue.

• 出版日期2012-12-7