Synthesis of highly functionalized furanones via aldol reaction of 3-silyloxyfurans |
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| Authors: | Winkler Jeffrey D Oh Kyungsoo Asselin Sylvie M |
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| Institution: | Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104, USA. winkler@sas.upenn.edu |
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| Abstract: | 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-bicyclo2.2.1]heptan-3-one ring system, which represents the formal product of hetero Diels-Alder reaction of the furan with the aldehyde. |
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