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1-Iodo-1-selenoalkenes as versatile alkene 1,1-dianion equivalents. Novel connective approach towards the tetrahydropyran subunit of polycavernoside A

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Perez-Balado, C Marko, Istvan [UCL]

syn-Hydroalumination of 2,4,6-triisopropylphenylselanyl-1-alkynes with DIBAL-H followed by AI/I exchange with 1, afforded exclusively (E)-1-iodo-1-selenoalkenes in good yields. 1-Iodo-1-selenopropene 10 proved to be a convenient 1.1 dianion equivalent, leading to the stereodivergent synthesis of allylsilanes (Z)-6 and (E)-6. Adduct 3, an intermediate in the synthesis of the tetrahydropyran subunit of polycavernoside A, was efficiently synthesised from allyisilane (Z)-6 and aldehyde 7 via an intramolecular Sakurai cyclisation. (c) 2005 Elsevier Ltd. All rights reserved.

Document type Article de périodique (Journal article) – Article de recherche
Publication date 2006
Language Anglais
Journal information "Tetrahedron" - Vol. 62, no. 10, p. 2331-2349 (2006)
Peer reviewed yes
Publisher Pergamon-elsevier Science Ltd (Oxford)
issn 0040-4020
e-issn 1464-5416
Publication status Publié
Affiliation UCL
Keywords alkenes ; carbanions ; polyeavernoside A ; Sakurai cyclisation ; selenium
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Bibliographic reference Perez-Balado, C ; Marko, Istvan. 1-Iodo-1-selenoalkenes as versatile alkene 1,1-dianion equivalents. Novel connective approach towards the tetrahydropyran subunit of polycavernoside A. In: Tetrahedron, Vol. 62, no. 10, p. 2331-2349 (2006)
Permanent URL http://hdl.handle.net/2078.1/38628