Short stereoselective synthesis of α-substituted γ-lactams

Bhooma Raghavan, Rodney L. Johnson

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

A concise, stereoselective synthesis of α-substituted γ-lactams is reported. γ-Lactam scaffolds 2 and 3, possessing an Evans' chiral auxiliary and two types of N substituents, were successfully alkylated with different electrophiles to give α-substituted γ-lactams with reasonable diastereoselectivities. The use of a masked carboxymethyl function off the lactam nitrogen provided a convergent means to α-substituted γ-lactam dipeptide isosteres.

Original languageEnglish (US)
Pages (from-to)2151-2154
Number of pages4
JournalJournal of Organic Chemistry
Volume71
Issue number5
DOIs
StatePublished - Mar 5 2006

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