Homolytic 1,5-transfer of chiral organosilicon groups from an enoxy oxygen to an alkoxy oxygen—implications for mechanism

文献信息

发布日期 2003-04-16

DOI 10.1039/B302307A

影响因子 6.222

作者

Sonia M. Horvat, Sunggak Kim, Carl H. Schiesser

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摘要

Reaction of the optically active silanes, ((SSi)-(−)-6), formed by treatment of racemic 2-methylenecycloheptanone oxide with LDA followed by (R)-(+)-chloromethyl(1-naphthyl)phenylsilane, with tributyltin hydride under standard radical conditions affords (2R/2S)-[(S)-(methyl(1-naphthyl)phenylsilyloxy)methyl]cycloheptanone, (SSi)-(−)-7, providing strong evidence that homolytic 1,5-transfers of organosilicon groups from enoxy oxygen to alkoxy oxygen proceed with retention of configuration, most likely through a frontside attack mechanism rather than via a hypervalent intermediate.

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来源期刊

Chemical Communications

CiteScore: 8.6

自引率: 4.7%

年发文量: 2458

ChemComm publishes urgent research which is of outstanding significance and interest to experts in the field, while also appealing to the journal’s broad chemistry readership. Our communication format is ideally suited to short, urgent studies that are of such importance that they require accelerated publication. Our scope covers all topics in chemistry, and research at the interface of chemistry and other disciplines (such as materials science, nanoscience, physics, engineering and biology) where there is a significant novelty in the chemistry aspects. Major topic areas covered include: Analytical Chemistry Catalysis Chemical Biology and medicinal chemistry Computational Chemistry and Machine Learning Energy and sustainable chemistry Environmental Chemistry Green Chemistry Inorganic Chemistry Materials Chemistry Nanoscience Organic Chemistry Physical Chemistry Polymer Chemistry Supramolecular Chemistry

Homolytic 1,5-transfer of chiral organosilicon groups from an enoxy oxygen to an alkoxy oxygen—implications for mechanism

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