Dualistic Nature of the Mechanism of the Morita-Baylis-Hillman Reaction Probed by Electrospray Ionization Mass Spectrometry

被引：97

作者：

Amarante, Giovanni W. ^{[2
]}

Milagre, Humberto M. S. ^{[1
]}

Vaz, Boniek G. ^{[1
]}

Ferreira, Bruno R. Vilacha ^{[2
]}

Eberlin, Marcos N. ^{[1
]}

Coelho, Fernando ^{[2
]}

机构：

[1] Univ Estadual Campinas, ThoMSon Mass Spectrometry Lab, Inst Chem, UNICAMP, BR-13084971 Campinas, SP, Brazil

[2] Univ Estadual Campinas, Lab Synth Nat Prod & Drugs, Inst Chem, UNICAMP, BR-13084971 Campinas, SP, Brazil

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 08期

基金：

巴西圣保罗研究基金会;

关键词：

ACTIVATED DOUBLE-BONDS; STEREOSELECTIVE-SYNTHESIS; SERINE OCTAMER; HECK REACTION; NECIC ACID; ADDUCTS; CATALYSIS; ALDEHYDES; SUBSTITUTION; SYNTHONS;

D O I：

10.1021/jo802578t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The Morita-Baylis-Hillman (MBH) reaction allows chemists to form new a C-C bonds in a single-step straightforward manner and thus to construct densely functionalized molecules for further chemical manipulation. Using electrospray ionization for transferring ions directly from solution to the gas phase, and mass (and tandem mass) spectrometry for mass and structural assignments, new key intermediates for the rate-determining step of the MBH reaction have been successfully intercepted and structurally characterized. These ESI-MS data provide experimental evidence supporting recent suggestions, based on kinetic experiments and theoretical calculations, for the dualist nature of the proton-transfer step of the MBH mechanism.

引用

页码：3031 / 3037

页数：7

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