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

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

References

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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.