CHELATION CONTROLLED ALLYLATION OF ALDEHYDES WITH A CHIRAL ALLYLSILYLENE DERIVED FROM (-)-10-PHENYLPINANEDIOL

Article abstract of DOI:10.1016/S0957-4166(00)86230-8

The chiral allylsilylene prepared from (-)-10-phenylpinanediol reacts with chiral α-alkoxy aldehydes in the presence of stannic chloride to afford homoallylic alcohols with diastereofacial selectivity ratios as high as 100:0.The results are consistent with attack of the allylsilylene on the less hindered face of the chelated intermediate.Our preliminary studies on several silylenes prepared from bicyclo<3.1.1> systems revealed that substituent effects on the chiral auxiliary and the silicon atom play an important role in the selectivity of these unique compounds.