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Short stereoselective synthesis of alpha-substituted gamma-lactams.

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

SUBMITTER: Raghavan B 

PROVIDER: S-EPMC2562328 | biostudies-literature | 2006 Mar

REPOSITORIES: biostudies-literature

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Short stereoselective synthesis of alpha-substituted gamma-lactams.

Raghavan Bhooma B   Johnson Rodney L RL  

The Journal of organic chemistry 20060301 5

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