Regio- and stereoselective construction of γ-butenolides through phosphine-catalyzed substitution of Morita-Baylis-Hillman acetates: An organocatalytic allylic alkylation

Chang Woo Cho; Michael J. Krische

doi:10.1002/anie.200461381

Regio- and stereoselective construction of γ-butenolides through phosphine-catalyzed substitution of Morita-Baylis-Hillman acetates: An organocatalytic allylic alkylation

Chang Woo Cho
, Michael J. Krische

University of Texas at Austin

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

187 Scopus citations

Abstract

Hold the metal: Upon exposure of acetates 1 to substoichiometric quantities of triphenylphosphane in the presence of 2, regioselective metal-free allylic substitution occurs through a formal tandem S_N2′-S _N2′ substitution mechanism to provide γ-butenolides 3 with high levels of regio- and diastereocontrol (see scheme).

Original language	English
Pages (from-to)	6689-6691
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	43
Issue number	48
DOIs	https://doi.org/10.1002/anie.200461381
State	Published - 10 Dec 2004

Keywords

Allylic substitution
Butenolides
C-C coupling
Organocatalysis

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abstract = "Hold the metal: Upon exposure of acetates 1 to substoichiometric quantities of triphenylphosphane in the presence of 2, regioselective metal-free allylic substitution occurs through a formal tandem SN2′-S N2′ substitution mechanism to provide γ-butenolides 3 with high levels of regio- and diastereocontrol (see scheme).",

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AU - Krische, Michael J.

PY - 2004/12/10

Y1 - 2004/12/10

N2 - Hold the metal: Upon exposure of acetates 1 to substoichiometric quantities of triphenylphosphane in the presence of 2, regioselective metal-free allylic substitution occurs through a formal tandem SN2′-S N2′ substitution mechanism to provide γ-butenolides 3 with high levels of regio- and diastereocontrol (see scheme).

AB - Hold the metal: Upon exposure of acetates 1 to substoichiometric quantities of triphenylphosphane in the presence of 2, regioselective metal-free allylic substitution occurs through a formal tandem SN2′-S N2′ substitution mechanism to provide γ-butenolides 3 with high levels of regio- and diastereocontrol (see scheme).

KW - Allylic substitution

KW - Butenolides

KW - C-C coupling

KW - Organocatalysis

UR - https://www.scopus.com/pages/publications/10944264979

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DO - 10.1002/anie.200461381

M3 - Article

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AN - SCOPUS:10944264979

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 48

ER -

Regio- and stereoselective construction of γ-butenolides through phosphine-catalyzed substitution of Morita-Baylis-Hillman acetates: An organocatalytic allylic alkylation

Abstract

Keywords

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