A Stereoselective Cyclization Strategy for the Preparation of gamma-Lactams and Their Use in the Synthesis of alpha-Methyl-beta-Proline
Chemistry and Biochemistry
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.
JOURNAL OF ORGANIC CHEMISTRY
(2012). A Stereoselective Cyclization Strategy for the Preparation of gamma-Lactams and Their Use in the Synthesis of alpha-Methyl-beta-Proline. JOURNAL OF ORGANIC CHEMISTRY, 77(23), 10925-2202.
Available at: http://aquila.usm.edu/fac_pubs/7565