A convenient synthesis of L-α-vinylglycine from L-homoserine lactone

David B. Berkowitz; Marianne K. Smith

doi:10.1055/s-1996-4177

A convenient synthesis of L-α-vinylglycine from L-homoserine lactone

David B. Berkowitz, Marianne K. Smith

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

Abstract

A procedure for the synthesis of L-α-vinylglycine from L-homoserine lactone is described. The route developed is convenient (only one chromatography step is required) and efficient (72%; ≥95% optical yield over 4 steps). Key features include the use of acid-labile protecting groups for the amino (Boc) and carboxyl (diphenylmethyl ester) groups, and the use of the phenylselenolate equivalent derived from sodium borohydride and diphenyl diselenide for L-homoserine lactone cleavage.

Original language	English (US)
Pages (from-to)	39-41
Number of pages	3
Journal	Synthesis
Issue number	1
DOIs	https://doi.org/10.1055/s-1996-4177
State	Published - 1996

Keywords

L-homoserine lactone
L-α-vinylglycine
enantiocontrolled synthesis
phenylselenolate anion

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-1996-4177

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abstract = "A procedure for the synthesis of L-α-vinylglycine from L-homoserine lactone is described. The route developed is convenient (only one chromatography step is required) and efficient (72%; ≥95% optical yield over 4 steps). Key features include the use of acid-labile protecting groups for the amino (Boc) and carboxyl (diphenylmethyl ester) groups, and the use of the phenylselenolate equivalent derived from sodium borohydride and diphenyl diselenide for L-homoserine lactone cleavage.",

keywords = "L-homoserine lactone, L-α-vinylglycine, enantiocontrolled synthesis, phenylselenolate anion",

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year = "1996",

doi = "10.1055/s-1996-4177",

language = "English (US)",

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journal = "Synthesis (Germany)",

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AU - Berkowitz, David B.

AU - Smith, Marianne K.

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N2 - A procedure for the synthesis of L-α-vinylglycine from L-homoserine lactone is described. The route developed is convenient (only one chromatography step is required) and efficient (72%; ≥95% optical yield over 4 steps). Key features include the use of acid-labile protecting groups for the amino (Boc) and carboxyl (diphenylmethyl ester) groups, and the use of the phenylselenolate equivalent derived from sodium borohydride and diphenyl diselenide for L-homoserine lactone cleavage.

AB - A procedure for the synthesis of L-α-vinylglycine from L-homoserine lactone is described. The route developed is convenient (only one chromatography step is required) and efficient (72%; ≥95% optical yield over 4 steps). Key features include the use of acid-labile protecting groups for the amino (Boc) and carboxyl (diphenylmethyl ester) groups, and the use of the phenylselenolate equivalent derived from sodium borohydride and diphenyl diselenide for L-homoserine lactone cleavage.

KW - L-homoserine lactone

KW - L-α-vinylglycine

KW - enantiocontrolled synthesis

KW - phenylselenolate anion

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A convenient synthesis of L-α-vinylglycine from L-homoserine lactone

Abstract

Keywords

ASJC Scopus subject areas

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