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

Access to Document

10.1055/s-1996-4177

Fingerprint Dive into the research topics of 'A convenient synthesis of L-α-vinylglycine from L-homoserine lactone'. Together they form a unique fingerprint.

Cite this

@article{1ea8bcec077840029e9d31de8b720b95,

title = "A convenient synthesis of L-α-vinylglycine from L-homoserine lactone",

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",

author = "Berkowitz, {David B.} and Smith, {Marianne K.}",

year = "1996",

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

language = "English (US)",

pages = "39--41",

journal = "Synthesis (Germany)",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "1",

}

TY - JOUR

T1 - A convenient synthesis of L-α-vinylglycine from L-homoserine lactone

AU - Berkowitz, David B.

AU - Smith, Marianne K.

PY - 1996

Y1 - 1996

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

UR - http://www.scopus.com/inward/record.url?scp=0030019887&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0030019887&partnerID=8YFLogxK

U2 - 10.1055/s-1996-4177

DO - 10.1055/s-1996-4177

M3 - Article

C2 - 29962541

AN - SCOPUS:0030019887

SP - 39

EP - 41

JO - Synthesis (Germany)

JF - Synthesis (Germany)

SN - 0039-7881

IS - 1

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Cite this