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.

BF<sub>3</sub>.OEt<sub>2</sub>-Mediated Benzylation of Arenes and Heteroarenes with Benzyl Ether Derivatives

“…1-Benzyl-4-methoxybenzene (3f) [36] and 1-benzyl-2methoxybenzene (4d) [15] (3f/4d = 5:1), liquid. 3f: 1 2-Benzylnaphthalene (3i) [37] and 1-benzylnaphthalene (4f) 14 (3i/4f =3:1), liquid. 3i: 1 di-p-Tolylmethane (3m) [40] and o-tolyl(p-tolyl)methane (4i) [19] (3m/4i = 5:3), liquid.…”