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
Masterson, D. S.
(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.
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