Issue 23, 2011
From the journal:

Chemical Communications

On the mechanism of the aza-Morita–Baylis–Hillman reaction: ESI-MS interception of a unique new intermediate†

Thais Regiani,ab   Vanessa G. Santos,b   Marla N. Godoi,b   Boniek G. Vaz,b   Marcos N. Eberlin*b  and  Fernando Coelho*a  

* Corresponding authors

a Laboratory of Synthesis of Natural Products and Drugs, University of Campinas-UNICAMP, Campinas, SP, Brazil
E-mail: coelho@iqm.unicamp.br

b ThoMSon Mass Spectrometry Laboratory, University of Campinas-UNICAMP, Campinas, SP, Brazil
E-mail: eberlin@iqm.unicamp.br

Abstract

Solutions of aza-Morita–Baylis–Hillman (aza-MBH) reactions were directly monitored by ESI(+)-MS(/MS) spectrometry to obtain information on their mechanism. A unique bis-sulfonamide intermediate was intercepted and characterized and, based on this novel species, a mechanism that rationalizes the uniqueness of aza-MBH reactions is proposed.

Graphical abstract: On the mechanism of the aza-Morita–Baylis–Hillman reaction: ESI-MS interception of a unique new intermediate

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Article information

DOI
https://doi.org/10.1039/C1CC10678C
Article type
Communication
Submitted
03 Feb 2011
Accepted
08 Apr 2011
First published
03 May 2011

Chem. Commun., 2011,47, 6593-6595

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On the mechanism of the aza-Morita–Baylis–Hillman reaction: ESI-MS interception of a unique new intermediate

T. Regiani, V. G. Santos, M. N. Godoi, B. G. Vaz, M. N. Eberlin and F. Coelho, Chem. Commun., 2011, 47, 6593 DOI: 10.1039/C1CC10678C

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