Dearomatising cyclisation of lithiated allyl phenyl ethers: The role of an oxazoline substituent

Rebecca A. Harvey; Ol'Ga Karlubíková; Sean Parris; Jonathan Clayden

doi:10.1016/j.tetlet.2013.05.098

Dearomatising cyclisation of lithiated allyl phenyl ethers: The role of an oxazoline substituent

Rebecca A. Harvey, Ol'Ga Karlubíková, Sean Parris, Jonathan Clayden^*

^*Corresponding author for this work

School of Chemistry

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

4 Citations (Scopus)

Abstract

Treatment of 3-allyloxyphenyl oxazolines with organolithium bases leads to allyllithiums which undergo dearomatising cyclisation. The resulting dearomatised anions may be quenched with electrophiles to form partially saturated benzopyran derivatives.

Original language	English
Pages (from-to)	4064-4066
Number of pages	3
Journal	Tetrahedron Letters
Volume	54
Issue number	31
Early online date	31 May 2013
DOIs	https://doi.org/10.1016/j.tetlet.2013.05.098
Publication status	Published - 31 Jul 2013

Keywords

Allyllithium
Cyclisation
Dearomatisation
Oxazoline
Synthesis

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title = "Dearomatising cyclisation of lithiated allyl phenyl ethers: The role of an oxazoline substituent",

abstract = "Treatment of 3-allyloxyphenyl oxazolines with organolithium bases leads to allyllithiums which undergo dearomatising cyclisation. The resulting dearomatised anions may be quenched with electrophiles to form partially saturated benzopyran derivatives.",

keywords = "Allyllithium, Cyclisation, Dearomatisation, Oxazoline, Synthesis",

author = "Harvey, {Rebecca A.} and Ol'Ga Karlub{\'i}kov{\'a} and Sean Parris and Jonathan Clayden",

year = "2013",

month = jul,

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doi = "10.1016/j.tetlet.2013.05.098",

language = "English",

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T1 - Dearomatising cyclisation of lithiated allyl phenyl ethers

T2 - The role of an oxazoline substituent

AU - Harvey, Rebecca A.

AU - Karlubíková, Ol'Ga

AU - Parris, Sean

AU - Clayden, Jonathan

PY - 2013/7/31

Y1 - 2013/7/31

N2 - Treatment of 3-allyloxyphenyl oxazolines with organolithium bases leads to allyllithiums which undergo dearomatising cyclisation. The resulting dearomatised anions may be quenched with electrophiles to form partially saturated benzopyran derivatives.

AB - Treatment of 3-allyloxyphenyl oxazolines with organolithium bases leads to allyllithiums which undergo dearomatising cyclisation. The resulting dearomatised anions may be quenched with electrophiles to form partially saturated benzopyran derivatives.

KW - Allyllithium

KW - Cyclisation

KW - Dearomatisation

KW - Oxazoline

KW - Synthesis

UR - http://www.scopus.com/inward/record.url?scp=84879686447&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2013.05.098

DO - 10.1016/j.tetlet.2013.05.098

M3 - Article (Academic Journal)

AN - SCOPUS:84879686447

SN - 0040-4039

VL - 54

SP - 4064

EP - 4066

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 31

ER -

Dearomatising cyclisation of lithiated allyl phenyl ethers: The role of an oxazoline substituent

Abstract

Keywords

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