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

K Miyakawa, T Konakahara, N Sakai…

Index: Miyakawa, Kenichi; Konakahara, Takeo; Sakai, Norio; Kozawa, Kozo; Gunji, Takahiro; Nagao, Yukinori Journal of Chemical Research, 2009 , # 1 p. 46 - 51

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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.