J. Panek, R. Beresis
Feb 1, 1993
Citations
0
Influential Citations
41
Citations
Journal
Journal of Organic Chemistry
Abstract
Methyl α-methyl-β-(dimethylphenylsilyl)-(E)-hex-4-enoates (2S,3R)-1a undergo BF 3 -OEt 2 -promoted additions with (S)-2-(benzyloxy)propanal (2) producing nearly enantiomerically pure cis-2,5-substituted tetrahydrofurans 3 whereas the reactions run under chelation controlled conditions employing SnCl 4 resulted in the formation of the complementary trans-2,5-disubstituted tetrahydrofuran. Additions to the enantiomeric silane (2R,3S)-1b utilizing BF 3 -OEt 2 or SnCl 4 afforded the cis-2,5-disubstituted furan stereochemistry in both cases