Synthesis of novel silyl enol ethers from chlorodimethyl(naphthylphenylmethyl)silanes having a chiral centre and a ketone and their chirality transfer effects in crossed-aldol reactions

Abstract

X-ray crystallography was used to determine the stereo structure of a novel chiral organosilicon compound, (2R)-(–)-(1-cyclohexenyloxy)dimethyl(1-naphthylphenylmethyl) silane, which has a chiral centre next to the silicon atom. The crossed-aldol reaction of the silyl enol ether with benzaldehyde gave the corresponding aldol products with high chirality transfer.