2-Alkenyl dioxolanylium cations, new reactive dienophiles in low temperature asymmetric Diels-Alder reactions

Chiral orthoesters 14–22 were prepared by an exchange reaction with orthoester 13. These compounds, after treatment with trimethylsilytriflate or tin(IV) chloride, gave rise to vinyl dioxolanylium cations which proved to be very reactive dienophiles in various Diels-Alder reactions. Graphic

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Bibliographic Details
Published in:Tetrahedron: asymmetry 1997-01, Vol.8 (1), p.139-148
Main Authors: Haudrechy, Arnaud, Picoul, Willy, Langlois, Yves
Format: Article
Language:English
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Summary:Chiral orthoesters 14–22 were prepared by an exchange reaction with orthoester 13. These compounds, after treatment with trimethylsilytriflate or tin(IV) chloride, gave rise to vinyl dioxolanylium cations which proved to be very reactive dienophiles in various Diels-Alder reactions. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(96)00470-3