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A highly stereoselective synthesis of chiral alpha-amino-beta-lactams via the Kinugasa reaction employing ynamides.

ABSTRACT: A highly stereoselective synthesis of chiral alpha-amino-beta-lactam through an ynamide-Kinugasa reaction is described. In addition, a mechanistic model is illustrated here to rationalize the observed diastereoselectivity, which depends on both the initial [3 + 2] cycloaddition step and the subsequent protonation for which both are highly selective.

SUBMITTER: Zhang X

PROVIDER: S-EPMC2587087 | biostudies-literature | 2008 Aug

REPOSITORIES: biostudies-literature

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A highly stereoselective synthesis of chiral alpha-amino-beta-lactams via the Kinugasa reaction employing ynamides.

Zhang Xuejun X Hsung Richard P RP Li Hongyan H Zhang Yu Y Johnson Whitney L WL Figueroa Ruth R

Organic letters 20080710 16

A highly stereoselective synthesis of chiral alpha-amino-beta-lactam through an ynamide-Kinugasa reaction is described. In addition, a mechanistic model is illustrated here to rationalize the observed diastereoselectivity, which depends on both the initial [3 + 2] cycloaddition step and the subsequent protonation for which both are highly selective. ...[more]

PMID: 18613692

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