Amino Acid Sulfinate Salts as Alkyl Radical Precursors

Joshua M. Hammond; Michael G. Gardiner; Lara R. Malins

doi:10.1021/acs.orglett.3c01112

Amino Acid Sulfinate Salts as Alkyl Radical Precursors

Joshua M. Hammond, Michael G. Gardiner, Lara R. Malins^*

^*Corresponding author for this work

Research School of Chemistry

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

1 Citation (Scopus)

Abstract

A general approach to the synthesis of amino acid sulfinate salts from commercially available α-chiral hydroxylated amino acids is reported. These reagents are shown to be valuable precursors to alkyl radicals under mild photochemical oxidation conditions. The photochemically generated amino acid radicals engage readily with alkyl and aryl disulfide radical traps to afford a diverse suite of modified amino acids.

Original language	English
Pages (from-to)	3157-3162
Number of pages	6
Journal	Organic Letters
Volume	25
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.3c01112
Publication status	Published - 5 May 2023

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title = "Amino Acid Sulfinate Salts as Alkyl Radical Precursors",

abstract = "A general approach to the synthesis of amino acid sulfinate salts from commercially available α-chiral hydroxylated amino acids is reported. These reagents are shown to be valuable precursors to alkyl radicals under mild photochemical oxidation conditions. The photochemically generated amino acid radicals engage readily with alkyl and aryl disulfide radical traps to afford a diverse suite of modified amino acids.",

author = "Hammond, {Joshua M.} and Gardiner, {Michael G.} and Malins, {Lara R.}",

note = "Publisher Copyright: {\textcopyright} 2023 American Chemical Society",

year = "2023",

month = may,

day = "5",

doi = "10.1021/acs.orglett.3c01112",

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T1 - Amino Acid Sulfinate Salts as Alkyl Radical Precursors

AU - Hammond, Joshua M.

AU - Gardiner, Michael G.

AU - Malins, Lara R.

PY - 2023/5/5

Y1 - 2023/5/5

N2 - A general approach to the synthesis of amino acid sulfinate salts from commercially available α-chiral hydroxylated amino acids is reported. These reagents are shown to be valuable precursors to alkyl radicals under mild photochemical oxidation conditions. The photochemically generated amino acid radicals engage readily with alkyl and aryl disulfide radical traps to afford a diverse suite of modified amino acids.

AB - A general approach to the synthesis of amino acid sulfinate salts from commercially available α-chiral hydroxylated amino acids is reported. These reagents are shown to be valuable precursors to alkyl radicals under mild photochemical oxidation conditions. The photochemically generated amino acid radicals engage readily with alkyl and aryl disulfide radical traps to afford a diverse suite of modified amino acids.

UR - http://www.scopus.com/inward/record.url?scp=85156243306&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.3c01112

DO - 10.1021/acs.orglett.3c01112

M3 - Article

SN - 1523-7060

VL - 25

SP - 3157

EP - 3162

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

Amino Acid Sulfinate Salts as Alkyl Radical Precursors

Abstract

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