Use of alkyl 2,4,6-triisopropylbenzoates in the asymmetric homologation of challenging boronic esters

Robin Larouche-Gauthier; Catherine J. Fletcher; Irantzu Couto; Varinder K. Aggarwal

doi:10.1039/c1cc14469c

Use of alkyl 2,4,6-triisopropylbenzoates in the asymmetric homologation of challenging boronic esters

Robin Larouche-Gauthier, Catherine J. Fletcher, Irantzu Couto, Varinder K. Aggarwal^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

70 Citations (Scopus)

Abstract

(-)-Sparteine induced lithiation of primary 2,4,6-triisopropylbenzoates and subsequent homologation of boronic esters is reported. A comparative study with lithiated N,N-diisopropylcarbamates has demonstrated the superiority of the hindered benzoate.

Original language	English
Pages (from-to)	12592-12594
Number of pages	3
Journal	Chemical Communications
Volume	47
Issue number	47
DOIs	https://doi.org/10.1039/c1cc14469c
Publication status	Published - 2011

Keywords

DIPOLE-STABILIZED CARBANIONS
(+)-SPARTEINE SURROGATE
CHIRAL CARBENOIDS
SULFUR YLIDES
ORGANOBORANES
REARRANGEMENT
LITHIATION
BORANES

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NEW ASSYMETRIC REACTIONS AND THEIR APPLICATION IN TOTAL SYNTHESIS
Aggarwal, V. K. (Principal Investigator)
1/10/05 → 1/10/10
Project: Research

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title = "Use of alkyl 2,4,6-triisopropylbenzoates in the asymmetric homologation of challenging boronic esters",

abstract = "(-)-Sparteine induced lithiation of primary 2,4,6-triisopropylbenzoates and subsequent homologation of boronic esters is reported. A comparative study with lithiated N,N-diisopropylcarbamates has demonstrated the superiority of the hindered benzoate.",

keywords = "DIPOLE-STABILIZED CARBANIONS, (+)-SPARTEINE SURROGATE, CHIRAL CARBENOIDS, SULFUR YLIDES, ORGANOBORANES, REARRANGEMENT, LITHIATION, BORANES",

author = "Robin Larouche-Gauthier and Fletcher, {Catherine J.} and Irantzu Couto and Aggarwal, {Varinder K.}",

year = "2011",

doi = "10.1039/c1cc14469c",

language = "English",

volume = "47",

pages = "12592--12594",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "47",

}

TY - JOUR

T1 - Use of alkyl 2,4,6-triisopropylbenzoates in the asymmetric homologation of challenging boronic esters

AU - Larouche-Gauthier, Robin

AU - Fletcher, Catherine J.

AU - Couto, Irantzu

AU - Aggarwal, Varinder K.

PY - 2011

Y1 - 2011

N2 - (-)-Sparteine induced lithiation of primary 2,4,6-triisopropylbenzoates and subsequent homologation of boronic esters is reported. A comparative study with lithiated N,N-diisopropylcarbamates has demonstrated the superiority of the hindered benzoate.

AB - (-)-Sparteine induced lithiation of primary 2,4,6-triisopropylbenzoates and subsequent homologation of boronic esters is reported. A comparative study with lithiated N,N-diisopropylcarbamates has demonstrated the superiority of the hindered benzoate.

KW - DIPOLE-STABILIZED CARBANIONS

KW - (+)-SPARTEINE SURROGATE

KW - CHIRAL CARBENOIDS

KW - SULFUR YLIDES

KW - ORGANOBORANES

KW - REARRANGEMENT

KW - LITHIATION

KW - BORANES

U2 - 10.1039/c1cc14469c

DO - 10.1039/c1cc14469c

M3 - Article (Academic Journal)

C2 - 21892499

SN - 1359-7345

VL - 47

SP - 12592

EP - 12594

JO - Chemical Communications

JF - Chemical Communications

IS - 47

ER -

Use of alkyl 2,4,6-triisopropylbenzoates in the asymmetric homologation of challenging boronic esters

Abstract

Keywords

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NEW ASSYMETRIC REACTIONS AND THEIR APPLICATION IN TOTAL SYNTHESIS

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