Homolytic 1,5-transfer of chiral organosilicon groups from an enoxy oxygen to an alkoxy oxygen--implications for mechanism.
Chem Commun (Camb)
; (10): 1182-3, 2003 May 21.
Article
em En
| MEDLINE
| ID: mdl-12778725
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)-phensylsilyloxy)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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MEDLINE
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En
Ano de publicação:
2003
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Article