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Synlett 2010(7): 1047-1050
DOI: 10.1055/s-0029-1219577
DOI: 10.1055/s-0029-1219577
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
The First One-Pot Synthesis of Morita-Baylis-Hillman Adducts Starting Directly from Alcohols
Further Information
Publication History
Received
5 January 2010
Publication Date:
10 March 2010 (online)


Abstract
The first example of one-pot oxidative carbon-carbon bond formation via the Morita-Baylis-Hillman reaction using alcohols is reported. The protocol involves silica gel-DABCO catalyzed oxidation of alcohols to aldehydes with chloramine-T followed by their Morita-Baylis-Hillman reaction with acrylonitrile or methyl acrylate to give 70-87% overall yields of the corresponding Morita-Baylis-Hillman adducts. The present work opens up a new and efficient synthetic route to Morita-Baylis-Hillman adducts directly from alcohols in a one-pot operation.
Key words
oxidation - C-C bond formation - alcohols - chloramine-T - silica gel-DABCO - Morita-Baylis-Hillman adducts