Enantioselective hydrogen-atom abstraction by homochiral silanethiyl radicals

(2S,5S)-trans-2,5- Dimethyl-1- phenyl-1- silacyclopentane-1- thiyl radicals abstract hydrogen enantioselectively from silicon in (±)-trans-2,5- dimethyl-1- phenyl-1- silacyclopentane to bring about kinetic resolution of the latter; the enantiomerically-enriched silyl radicals so produced are trapped...

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Bibliographic Details
Published inTetrahedron letters Vol. 36; no. 21; pp. 3731 - 3734
Main Authors Dang, Hai-Shan, Roberts, Brian P.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 22.05.1995
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
AMINE-BORYL RADICALS
HOMOLYTIC REACTIONS
LIGATED BORANES
ESTERS
ALKYLBORANES
TRIETHYLSILANE
POLARITY REVERSAL CATALYSTS
ALKYL-HALIDES
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Summary:(2S,5S)-trans-2,5- Dimethyl-1- phenyl-1- silacyclopentane-1- thiyl radicals abstract hydrogen enantioselectively from silicon in (±)-trans-2,5- dimethyl-1- phenyl-1- silacyclopentane to bring about kinetic resolution of the latter; the enantiomerically-enriched silyl radicals so produced are trapped by alkyl bromide to give optically active bromosilane. The (2 S,5 S)-(+)-enantiomer of 1 is the more reactive.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(95)00566-U