STEREOCHEMISTRY AND MECHANISM OF ASYMMETRIC ALLYLATION OF ALDEHYDES WITH OPTICALLY ACTIVE ALLYLSILICONATES

Article abstract of DOI:10.1016/S0040-4039(00)80841-2

Reaction of (R)-(Z)-1-phenyl-1-(triethoxysilyl)-2-butene (1) with benzaldehyde in the presence of catechol and triethylamine gave (3S,4R)-(E)-1,4-diphenyl-3-methyl-4-hydroxy-1-butene (3a) and (3S,4S) isomer (3b) in a ratio of 90 to 10, the stereochemistry indicating that the allylation proceeded via six-membered cyclic transition states.Allylation with (R)-(Z)-1-phenyl-1-(trifluorosilyl)-2-butene (10) in the presence of cesium fluoride also proceeded via six-membered transition states.