Cross metathesis-mediated synthesis of hydroxamic acid derivatives

An alternative synthesis of α,ß-unsaturated hydroxamates via cross metathesis between a class-I olefin and -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 substrate...

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Bibliographic Details
Published in:	Beilstein journal of organic chemistry Vol. 14; no. 1; pp. 3070 - 3075
Main Authors:	Chattopadhyay, Shital Kumar, Ghosh, Subhankar, Sil, Suman
Format:	Journal Article
Language:	English
Published:	Germany Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 17-12-2018 Beilstein-Institut
Subjects:	Amino acids Cancer catalysis Chemistry Chromatography cross metathesis Full Research Paper Hydrogenation hydroxamates Hydroxamic acid Peptides α-amino acid West Bengal India catalysis hydroxamates α-amino acid cross metathesis
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Summary:	An alternative synthesis of α,ß-unsaturated hydroxamates via cross metathesis between a class-I olefin and -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.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1860-5397 2195-951X 1860-5397
DOI:	10.3762/bjoc.14.285