Synthesis 2007(3): 433-441  
DOI: 10.1055/s-2007-965880
PAPER
© Georg Thieme Verlag Stuttgart · New York

Novel Boronic Acid Mannich Reactions of α,α-Dichloro- and α,α,ω-Tri­chloro­aldehydes with Arylboronic Acids

Sara Stas, Kourosch Abbaspour Tehrani*
Department of Organic Chemistry, Vrije Universiteit Brussel, Pleinlaan 2, 1050 Brussels, Belgium
Fax: +32(2)6293304; e-Mail: Kourosch.abbaspour.tehrani@vub.ac.be;
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Publikationsverlauf

Received 6 September 2006
Publikationsdatum:
12. Januar 2007 (online)

Abstract

A novel variation of the boronic acid Mannich (BAM) reaction is described, in which α,α-dichloro- and α,α,ω-trichloroaldehydes, morpholine, and arylboronic acids are used. During this one-pot reaction in refluxing toluene, 1-phenyl-1-morpholinoalkan-2-ones form in moderate yields. The dichloromethylene group is formally converted into a ketone functionality and as such acts as a masked carbonyl group.

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Abbaspour Tehrani, K.; Stas, S. unpublished results.