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

Thais Regiani; Vanessa G Santos; Marla N Godoi; Boniek G Vaz; Marcos N Eberlin; Fernando Coelho

doi:10.1039/c1cc10678c

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

Chem Commun (Camb). 2011 Jun 21;47(23):6593-5. doi: 10.1039/c1cc10678c. Epub 2011 May 3.

Authors

Thais Regiani¹, Vanessa G Santos, Marla N Godoi, Boniek G Vaz, Marcos N Eberlin, Fernando Coelho

Affiliation

¹ Laboratory of Synthesis of Natural Products and Drugs, University of Campinas-UNICAMP, Campinas, SP, Brazil.

PMID: 21541415
DOI: 10.1039/c1cc10678c

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.

MeSH terms

Aza Compounds / chemistry*
Imines / chemistry
Spectrometry, Mass, Electrospray Ionization
Sulfonamides / chemistry

Substances

Aza Compounds
Imines
Sulfonamides