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

文献情報

出版日 2003-04-16

DOI 10.1039/B302307A

インパクトファクター 6.222

著者

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

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要旨

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.

掲載誌

Chemical Communications

CiteScore: 8.6

自己引用率: 4.7%

年間論文数: 2458

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

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