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.
Winkler
Jeffrey D
JD
Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104, USA. winkler@sas.upenn.edu
Oh
Kyungsoo
K
Asselin
Sylvie M
SM
D000447:Aldehydes / Q000737:chemistry; D001974:Bromosuccinimide; D018360:Crystallography, X-Ray; D003500:Cyclization; D005663:Furans / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D005663:Furans; D001974:Bromosuccinimide