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Synthesis 2006(6): 946-948  
DOI: 10.1055/s-2006-926366
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Tandem β-Elimination-Morita-Baylis-Hillman Reaction in α,β-Unsaturated Sugar Aldehydes

Pilar Areces*a, Esther Carrascoa, Alicia Manchaa, Joaquín Plumet*b
a Universidad de Extremadura, Facultad de Ciencias, Departamento de Química Orgánica, 06071 Badajoz, Spain
Fax: +34(92)4289309030; e-Mail: pareces@unex.es;
b Universidad Complutense, Facultad de Química, Departamento de Química Orgánica, 28040 Madrid, Spain
Fax: +34(91)3944100; e-Mail: plumety@quim.ucm.es;
Further Information

Publication History

Received 23 September 2005
Publication Date:
27 February 2006 (online)

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Abstract

The first Morita-Baylis-Hillman reaction of a 1-formylbutadiene derivative is reported. In addition, a convenient synthesis of 2-acetoxy-4-formylbutadiene derivatives starting from easily available d-galactal and d-arabinal is also described.

Key words

DABCO - functionalized dienes - Morita-Baylis-Hillman reaction - unsaturated sugar aldehydes

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6

Deprotonation at position 4 in compound 3 to give a conjugate carbanion followed by departure of the acetoxy group (E1cB mechanism) at position 5 appears to be the most probable reaction path. See ref. 5.