Organolithium additions to styrene derivatives .3. Enantioselective routes to 2-arylalkanoic acids

X D  Wei; R J K  Taylor

Organolithium additions to styrene derivatives .3. Enantioselective routes to 2-arylalkanoic acids

Chemistry

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

Abstract

Organolithium addition to styrene and its derivatives, followed by electrophilic trapping, has been investigated in the presence of (-)-sparteine. With styrene, enantiomeric excesses up to 30% were observed, the ee depending on the solvent, temperature and electrophile. With 2-substituted styrenes, butyllithium addition followed by carboxylation gave a range of 2-arylheptanoic acids with ee's up to 72% (with 2-methoxystyrene in cumene at -95 degrees C). (C) 1997 Elsevier Science Ltd.

Original language	English
Pages (from-to)	665-668
Number of pages	4
Journal	TETRAHEDRON-ASYMMETRY
Volume	8
Issue number	5
Publication status	Published - 13 Mar 1997

Keywords

ORGANOMETALLIC REAGENTS
(-)-SPARTEINE

Cite this

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title = "Organolithium additions to styrene derivatives .3. Enantioselective routes to 2-arylalkanoic acids",

abstract = "Organolithium addition to styrene and its derivatives, followed by electrophilic trapping, has been investigated in the presence of (-)-sparteine. With styrene, enantiomeric excesses up to 30% were observed, the ee depending on the solvent, temperature and electrophile. With 2-substituted styrenes, butyllithium addition followed by carboxylation gave a range of 2-arylheptanoic acids with ee's up to 72% (with 2-methoxystyrene in cumene at -95 degrees C). (C) 1997 Elsevier Science Ltd.",

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T1 - Organolithium additions to styrene derivatives .3. Enantioselective routes to 2-arylalkanoic acids

AU - Wei, X D

AU - Taylor, R J K

PY - 1997/3/13

Y1 - 1997/3/13

N2 - Organolithium addition to styrene and its derivatives, followed by electrophilic trapping, has been investigated in the presence of (-)-sparteine. With styrene, enantiomeric excesses up to 30% were observed, the ee depending on the solvent, temperature and electrophile. With 2-substituted styrenes, butyllithium addition followed by carboxylation gave a range of 2-arylheptanoic acids with ee's up to 72% (with 2-methoxystyrene in cumene at -95 degrees C). (C) 1997 Elsevier Science Ltd.

AB - Organolithium addition to styrene and its derivatives, followed by electrophilic trapping, has been investigated in the presence of (-)-sparteine. With styrene, enantiomeric excesses up to 30% were observed, the ee depending on the solvent, temperature and electrophile. With 2-substituted styrenes, butyllithium addition followed by carboxylation gave a range of 2-arylheptanoic acids with ee's up to 72% (with 2-methoxystyrene in cumene at -95 degrees C). (C) 1997 Elsevier Science Ltd.

KW - ORGANOMETALLIC REAGENTS

KW - (-)-SPARTEINE

M3 - Article

SN - 0957-4166

VL - 8

SP - 665

EP - 668

JO - TETRAHEDRON-ASYMMETRY

JF - TETRAHEDRON-ASYMMETRY

IS - 5

ER -