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-Reference-Cited by-同舟云学术

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

Published:2009-01 Issue:1 Volume:2009 Page:46-51
ISSN:1747-5198
Container-title:Journal of Chemical Research
language:en
Short-container-title:Journal of Chemical Research

Author:

Miyakawa Kenichi¹,Konakahara Takeo¹,Sakai Norio¹,Kozawa Kozo¹,Gunji Takahiro¹,Nagao Yukinori¹

Affiliation:

1. Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science (RIKADAI), Noda, Chiba 278-8510, Japan

Abstract

X-ray crystallography was used to determine the stereo structure of a novel chiral organosilicon compound, (2 R)-(–)-(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.

Publisher

SAGE Publications

Subject

General Chemistry

Link

http://journals.sagepub.com/doi/pdf/10.3184/030823409X393709

Reference15 articles.

1. Silanes in organic synthesis. 19. Examination of (-)-.alpha.-naphthylphenylmethylallylsilane as a template for effecting chirality transfer from silicon to carbon

2. Stereochemical studies of fluoride ion-assisted reductions of ketones by organosilicon hydrides

3. New cross-aldol reactions. Reactions of silyl enol ethers with carbonyl compounds activated by titanium tetrachloride

4. Chirality transfer from silicon to carbon: use of optically pure cyclic silanes with a binaphthalene chiral unit

5. Silicon-Stereogenic Silanes in Asymmetric Catalysis

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1. ChemInform Abstract: Synthesis of Novel Silyl Enol Ethers from Chlorodimethyl(naphthylphenylmethyl)silanes Having a Chiral Center and a Ketone and Their Chirality Transfer Effects in Crossed-Aldol Reactions.;ChemInform;2009-06-23