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

Laboratory of Synthesis of Natural Products and Drugs, University of Campinas-UNICAMP, Campinas, SP, Brazil.
Chemical Communications (Impact Factor: 6.38). 06/2011; 47(23):6593-5. DOI: 10.1039/c1cc10678c
Source: PubMed

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.

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