Enantioselective organocatalytic aryloxylation of aldehydes with o-quinones

Felix A. Hernandez-Juan; Dane M. Cockfield; Darren J. Dixon

doi:10.1016/j.tetlet.2006.12.140

Enantioselective organocatalytic aryloxylation of aldehydes with o-quinones

Felix A. Hernandez-Juan, Dane M. Cockfield, Darren J. Dixon

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

Abstract

An enantioselective organocatalytic inverse electron demand hetero Diels-Alder reaction of in situ generated enamines with o-quinone reagents is reported. The method, which is optimal in wet acetonitrile at ambient temperature, provides a new and direct asymmetric route to the aryl alkyl ether motif and an alternative metal-free strategy to SN2 substitutions with phenolate nucleophiles. © 2007 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	1605-1608
Number of pages	3
Journal	Tetrahedron Letters
Volume	48
Issue number	9
DOIs	https://doi.org/10.1016/j.tetlet.2006.12.140
Publication status	Published - 26 Feb 2007

Keywords

Aryloxylation
Diels-Alder
Enamine
Enantioselective organocatalysis
o-Quinone

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10.1016/j.tetlet.2006.12.140

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title = "Enantioselective organocatalytic aryloxylation of aldehydes with o-quinones",

abstract = "An enantioselective organocatalytic inverse electron demand hetero Diels-Alder reaction of in situ generated enamines with o-quinone reagents is reported. The method, which is optimal in wet acetonitrile at ambient temperature, provides a new and direct asymmetric route to the aryl alkyl ether motif and an alternative metal-free strategy to SN2 substitutions with phenolate nucleophiles. {\textcopyright} 2007 Elsevier Ltd. All rights reserved.",

keywords = "Aryloxylation, Diels-Alder, Enamine, Enantioselective organocatalysis, o-Quinone",

author = "Hernandez-Juan, {Felix A.} and Cockfield, {Dane M.} and Dixon, {Darren J.}",

year = "2007",

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T1 - Enantioselective organocatalytic aryloxylation of aldehydes with o-quinones

AU - Hernandez-Juan, Felix A.

AU - Cockfield, Dane M.

AU - Dixon, Darren J.

PY - 2007/2/26

Y1 - 2007/2/26

N2 - An enantioselective organocatalytic inverse electron demand hetero Diels-Alder reaction of in situ generated enamines with o-quinone reagents is reported. The method, which is optimal in wet acetonitrile at ambient temperature, provides a new and direct asymmetric route to the aryl alkyl ether motif and an alternative metal-free strategy to SN2 substitutions with phenolate nucleophiles. © 2007 Elsevier Ltd. All rights reserved.

AB - An enantioselective organocatalytic inverse electron demand hetero Diels-Alder reaction of in situ generated enamines with o-quinone reagents is reported. The method, which is optimal in wet acetonitrile at ambient temperature, provides a new and direct asymmetric route to the aryl alkyl ether motif and an alternative metal-free strategy to SN2 substitutions with phenolate nucleophiles. © 2007 Elsevier Ltd. All rights reserved.

KW - Aryloxylation

KW - Diels-Alder

KW - Enamine

KW - Enantioselective organocatalysis

KW - o-Quinone

U2 - 10.1016/j.tetlet.2006.12.140

DO - 10.1016/j.tetlet.2006.12.140

M3 - Article

SN - 1873-3581

VL - 48

SP - 1605

EP - 1608

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 9

ER -

Enantioselective organocatalytic aryloxylation of aldehydes with o-quinones

Abstract

Keywords

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