Radical decarboxylative alkylation of tartaric acid

Derek H.R. Barton; Alice Gateau-Olesker; Stephan D. Géro; Brigitte Lacher; Catherine Tachdjian; Samir Z. Zard

doi:10.1016/S0040-4020(01)81288-6

Radical decarboxylative alkylation of tartaric acid

Derek H.R. Barton
, Alice Gateau-Olesker
, Stephan D. Géro
, Brigitte Lacher
, Catherine Tachdjian
, Samir Z. Zard

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

Abstract

New derivatives of L-(+)-tartaric acid have been synthesized from the monomethyl-2,3-O-isopropylidene (R,R)-(+)-tartrate by visible light photolysis of its N-hydroxy-2-thiopyridone ester derivative in presence of activated alkenes. The carbon radical generated at the dioxolane ring adds stereoselectively to olefins to give the addition products with retention of configuration.

Original language	English
Pages (from-to)	4589-4602
Number of pages	14
Journal	Tetrahedron
Volume	49
Issue number	21
DOIs	https://doi.org/10.1016/S0040-4020(01)81288-6
Publication status	Published - 21 May 1993
Externally published	Yes

Keywords

CC bond formation
N-Hydroxy-2-thiopyridone
Tartaric acid
radical decarboxylation
stereospecific alkylation.
visible light photolysis

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10.1016/S0040-4020(01)81288-6

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@article{e487c73c9d8042d6be2673355cd50d68,

title = "Radical decarboxylative alkylation of tartaric acid",

abstract = "New derivatives of L-(+)-tartaric acid have been synthesized from the monomethyl-2,3-O-isopropylidene (R,R)-(+)-tartrate by visible light photolysis of its N-hydroxy-2-thiopyridone ester derivative in presence of activated alkenes. The carbon radical generated at the dioxolane ring adds stereoselectively to olefins to give the addition products with retention of configuration.",

keywords = "CC bond formation, N-Hydroxy-2-thiopyridone, Tartaric acid, radical decarboxylation, stereospecific alkylation., visible light photolysis",

author = "Barton, \{Derek H.R.\} and Alice Gateau-Olesker and G{\'e}ro, \{Stephan D.\} and Brigitte Lacher and Catherine Tachdjian and Zard, \{Samir Z.\}",

year = "1993",

month = may,

day = "21",

doi = "10.1016/S0040-4020(01)81288-6",

language = "English",

volume = "49",

pages = "4589--4602",

journal = "Tetrahedron",

issn = "0040-4020",

number = "21",

}

TY - JOUR

T1 - Radical decarboxylative alkylation of tartaric acid

AU - Barton, Derek H.R.

AU - Gateau-Olesker, Alice

AU - Géro, Stephan D.

AU - Lacher, Brigitte

AU - Tachdjian, Catherine

AU - Zard, Samir Z.

PY - 1993/5/21

Y1 - 1993/5/21

N2 - New derivatives of L-(+)-tartaric acid have been synthesized from the monomethyl-2,3-O-isopropylidene (R,R)-(+)-tartrate by visible light photolysis of its N-hydroxy-2-thiopyridone ester derivative in presence of activated alkenes. The carbon radical generated at the dioxolane ring adds stereoselectively to olefins to give the addition products with retention of configuration.

AB - New derivatives of L-(+)-tartaric acid have been synthesized from the monomethyl-2,3-O-isopropylidene (R,R)-(+)-tartrate by visible light photolysis of its N-hydroxy-2-thiopyridone ester derivative in presence of activated alkenes. The carbon radical generated at the dioxolane ring adds stereoselectively to olefins to give the addition products with retention of configuration.

KW - CC bond formation

KW - N-Hydroxy-2-thiopyridone

KW - Tartaric acid

KW - radical decarboxylation

KW - stereospecific alkylation.

KW - visible light photolysis

U2 - 10.1016/S0040-4020(01)81288-6

DO - 10.1016/S0040-4020(01)81288-6

M3 - Article

AN - SCOPUS:0027208175

SN - 0040-4020

VL - 49

SP - 4589

EP - 4602

JO - Tetrahedron

JF - Tetrahedron

IS - 21

ER -

Radical decarboxylative alkylation of tartaric acid

Abstract

Keywords

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