Stereochemically divergent pathways for the allylation and crotylation reactions of anti- and syn-β-hydroxy-α-methyl aldehydes with allyl- and crotyltrifluorosilanes

Article abstract of DOI:10.1016/S0040-4039(99)00730-3

Allylation and crotylation reactions of 2,3-anti-β-hydroxy-α-methyl aldehydes 10 and 11 with allyl and crotyltrifluorosilanes 2, 8 and 9 proceed with high selectivity via the bicyclic chelated transition states 3 and 30. In contrast, analogous allylation