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Cross metathesis-mediated synthesis of hydroxamic acid derivatives.

ABSTRACT: An alternative synthesis of ?,ß-unsaturated hydroxamates via cross metathesis between a class-I olefin and N-benzyloxyacrylamide is reported. The reaction proceeds better in the presence of Grubbs' second generation catalyst within short time and in good yields (57-85%) with a range of substrates. Subsequent hydrogenation of each of the CM products delivers the title compounds in moderate to very good yield (70-89%). An important demonstration of the protocol is the preparation of the unusual amino acid component of the bioactive cyclic peptide Chap-31.

SUBMITTER: Chattopadhyay SK

PROVIDER: S-EPMC6317413 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Cross metathesis-mediated synthesis of hydroxamic acid derivatives.

Chattopadhyay Shital Kumar SK Ghosh Subhankar S Sil Suman S

Beilstein journal of organic chemistry 20181217

An alternative synthesis of α,ß-unsaturated hydroxamates via cross metathesis between a class-I olefin and <i>N</i>-benzyloxyacrylamide is reported. The reaction proceeds better in the presence of Grubbs' second generation catalyst within short time and in good yields (57-85%) with a range of substrates. Subsequent hydrogenation of each of the CM products delivers the title compounds in moderate to very good yield (70-89%). An important demonstration of the protocol is the preparation of the unu ...[more]

PMID: 30643583

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