Short stereoselective synthesis of α-substituted γ-lactams

Bhooma Raghavan; Rodney L. Johnson

doi:10.1021/jo052212q

Short stereoselective synthesis of α-substituted γ-lactams

Bhooma Raghavan
, Rodney L. Johnson

Medicinal Chemistry

Research output: Contribution to journal › Article › peer-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 language	English (US)
Pages (from-to)	2151-2154
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	71
Issue number	5
DOIs	https://doi.org/10.1021/jo052212q
State	Published - Mar 5 2006

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10.1021/jo052212q

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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.",

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N2 - 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.

AB - 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.

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Short stereoselective synthesis of α-substituted γ-lactams

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