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Pd-Catalyzed Acyl C-O Bond Activation for Selective Ring-Opening of ?-Methylene-?-lactones with Amines.

ABSTRACT: A Pd-catalyzed ring-opening of ?-lactones with various types of amines (primary, secondary, and aryl) to provide ?-hydroxy amides with excellent selectivity toward acyl C-O bond cleavage is reported. The utility of this protocol is demonstrated in an asymmetric kinetic resolution providing enantioenriched ?-methylene-?-lactones.

SUBMITTER: Malapit CA

PROVIDER: S-EPMC5839468 | biostudies-literature | 2017 Apr

REPOSITORIES: biostudies-literature

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Pd-Catalyzed Acyl C-O Bond Activation for Selective Ring-Opening of α-Methylene-β-lactones with Amines.

Malapit Christian A CA Caldwell Donald R DR Sassu Nicole N Milbin Samuel S Howell Amy R AR

Organic letters 20170404 8

A Pd-catalyzed ring-opening of β-lactones with various types of amines (primary, secondary, and aryl) to provide β-hydroxy amides with excellent selectivity toward acyl C-O bond cleavage is reported. The utility of this protocol is demonstrated in an asymmetric kinetic resolution providing enantioenriched α-methylene-β-lactones. ...[more]

PMID: 28375015

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