The michael addition of sulfur anions to β,β-substituted Nα-formyl-α,β-dehydroamino acid esters

C. Freeman Stanfield; Victor J. Hruby

doi:10.1080/00397918808060748

The michael addition of sulfur anions to β,β-substituted N^α-formyl-α,β-dehydroamino acid esters

C. Freeman Stanfield, Victor J. Hruby

Chemistry and Biochemistry

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

9 Scopus citations

Abstract

The addition of lithium benzylthiolates to N^α-formyl-α,β-dehydro-α-amino acid esters gave protected N^α-formyl-β-S-benzyl-β,S-dialkyl- cysteine esters. Hydrolysis and N^α-protection produced β,β-dialkyl-cysteines which can be used for peptide synthesis.

Original language	English (US)
Pages (from-to)	531-543
Number of pages	13
Journal	Synthetic Communications
Volume	18
Issue number	5
DOIs	https://doi.org/10.1080/00397918808060748
State	Published - Apr 1 1988

ASJC Scopus subject areas

Organic Chemistry

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10.1080/00397918808060748

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title = "The michael addition of sulfur anions to β,β-substituted Nα-formyl-α,β-dehydroamino acid esters",

abstract = "The addition of lithium benzylthiolates to Nα-formyl-α,β-dehydro-α-amino acid esters gave protected Nα-formyl-β-S-benzyl-β,S-dialkyl- cysteine esters. Hydrolysis and Nα-protection produced β,β-dialkyl-cysteines which can be used for peptide synthesis.",

author = "{Freeman Stanfield}, C. and Hruby, {Victor J.}",

note = "Funding Information: Acknowledgment: This work was supported by the National Science",

year = "1988",

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T1 - The michael addition of sulfur anions to β,β-substituted Nα-formyl-α,β-dehydroamino acid esters

AU - Freeman Stanfield, C.

AU - Hruby, Victor J.

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PY - 1988/4/1

Y1 - 1988/4/1

N2 - The addition of lithium benzylthiolates to Nα-formyl-α,β-dehydro-α-amino acid esters gave protected Nα-formyl-β-S-benzyl-β,S-dialkyl- cysteine esters. Hydrolysis and Nα-protection produced β,β-dialkyl-cysteines which can be used for peptide synthesis.

AB - The addition of lithium benzylthiolates to Nα-formyl-α,β-dehydro-α-amino acid esters gave protected Nα-formyl-β-S-benzyl-β,S-dialkyl- cysteine esters. Hydrolysis and Nα-protection produced β,β-dialkyl-cysteines which can be used for peptide synthesis.

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The michael addition of sulfur anions to β,β-substituted N^α-formyl-α,β-dehydroamino acid esters

Abstract

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