Synthesis of Quaternary Amino Acids Bearing a (2'Z)-fluorovinyl Alpha-branch: Potential PLP Enzyme Inactivators

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2004 May 21

PMID 15151423

Citations 17

Authors

David B Berkowitz

Roberto de la Salud-Bea

Wan-Jin Jahng

Affiliations

Soon will be listed here.

Abstract

Protected alpha-formyl amino acids, themselves available from the corresponding alpha-vinyl amino acids, are stereoselectively transformed into the (Z)-configured alpha-(2'-fluoro)vinyl amino acids via a three-step sequence. The route employs McCarthy's reagent, diethyl alpha-fluoro-alpha-(phenylsulfonyl)methyl phosphonate, and proceeds via the intermediate (E)-alpha-fluorovinyl sulfones and (E)-alpha-fluorovinylstannanes. The latter may either be exploited as novel cross-coupling partners for fluorovinyl branch extension or be globally deprotected, to provide the title compounds. [structure: see text]

Citing Articles

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Graham D, Beio M, Nelson D, Berkowitz D Front Mol Biosci. 2019; 6:8.

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