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Stereoselective synthesis of silacyclohexanols by silicon tethered Type II ene cyclisation

Abstract:
Vinyl silane precursors for intramolecular ene reaction were prepared either by sequential organometallic substitution of appropriate silyl halides or by ring opening of oxasilacyclopentanes with 2-propenyllithium. The oxasilacyclopentane intermediates were prepared by free-radical cyclisation, intramolecular hydrosilylation, or intramolecular Diels-Alder reaction. Treatment of the ene precursors with methylaluminium dichloride resulted in the formation of silacyclohexanols with high stereoselectivity. (C) 2000 Elsevier Science Ltd.
Publication status:
Published

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
O'Connor, G More by this author
Sardharwala, T More by this author
Middleton, DS More by this author
Journal:
TETRAHEDRON
Volume:
56
Issue:
42
Pages:
8309-8320
Publication date:
2000-10-13
DOI:
ISSN:
0040-4020
URN:
uuid:47927dca-503f-4f07-a709-ee79e0f73b18
Source identifiers:
55238
Local pid:
pubs:55238

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