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Issue 10, 2003
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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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Abstract

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.

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

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Article information


Submitted
27 Feb 2003
Accepted
28 Mar 2003
First published
16 Apr 2003

Chem. Commun., 2003, 1182-1183
Article type
Communication

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

S. M. Horvat, S. Kim and C. H. Schiesser, Chem. Commun., 2003, 1182
DOI: 10.1039/B302307A

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