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Winkler, J.D. et al.

Winkler, Oh, Asselin,

Synthesis of highly functionalized furanones via aldol reaction of 3-silyloxyfurans.

[reaction: see text] The stereoselective aldol reaction of 3-silyloxyfurans with aldehydes in the presence of a Lewis acid is described. N-Bromosuccinimide (NBS)-mediated cyclization of the aldol product leads to the formation of the 2,7-dioxa-bicyclo[2.2.1]heptan-3-one ring system, which represents the formal product of hetero Diels-Alder reaction of the furan with the aldehyde.[1]

References

Synthesis of highly functionalized furanones via aldol reaction of 3-silyloxyfurans. Winkler, J.D., Oh, K., Asselin, S.M. Org. Lett. (2005) [Pubmed]

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