10.1021/ol047810q.s001
Jeffrey D. Winkler
Jeffrey D.
Winkler
Kyungsoo Oh
Kyungsoo
Oh
Sylvie M. Asselin
Sylvie M.
Asselin
Synthesis of Highly Functionalized
Furanones via Aldol Reaction of
3-Silyloxyfurans<sup>†</sup>
American Chemical Society
2005
presence
furan
Silyloxyfuran
Diel
Bromosuccinimide
NBS
hetero
cyclization
aldehyde
Synthesi
Functionalized Furanones
silyloxyfuran
formation
Aldol Reaction
aldol product
stereoselective aldol reaction
Lewis acid
2005-02-03 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Synthesis_of_Highly_Functionalized_Furanones_via_Aldol_Reaction_of_3_Silyloxyfurans_sup_sup_/3302509
The stereoselective aldol reaction of 3-silyloxyfurans with aldehydes in the presence of a Lewis acid is described. <i>N</i>-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.