Issue 10, 2003
From the journal:

Chemical Communications

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

Sonia M. Horvat,a   Sunggak Kimb  and  Carl H. Schiesser*a  

* Corresponding authors

a School of Chemistry, Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria, Australia
E-mail: carlhs@unimelb.edu.au

b Department of Chemistry, Center for Molecular Design and Synthesis, School of Molecular Science (BK-21), Korea Advanced Institute of Science and Technology, Taejon 305-701, Korea

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

DOI
https://doi.org/10.1039/B302307A
Article type
Communication
Submitted
27 Feb 2003
Accepted
28 Mar 2003
First published
16 Apr 2003

Chem. Commun., 2003, 1182-1183

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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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