Site Selectivity and Regioselectivity of the Hetero-Diels-Alder and Cheletropic Additions of Sulfur-Dioxide to a 2,3,6,7-Tetramethylidenebicyclo[3.2.1]Octane Derivative
Deguin, B.; Vogel, P.
1993

Abstract

At -55-degrees-C SO2 adds to 4-[(tert-butyl)dimethylsilyloxy]-1-methoxy-2,3,6,7-tetramethylidenebicyc lo[3.2.1]octane reversibly and selectively onto the s-cis-butadiene moiety at C(2), C(3) giving a single regioisomeric sultine. At -45-degrees-C the cheletropic addition of SO2 occurs selectively giving the monosulfolene attached at C(2), C(3).

Details

Title Site Selectivity and Regioselectivity of the Hetero-Diels-Alder and Cheletropic Additions of Sulfur-Dioxide to a 2,3,6,7-Tetramethylidenebicyclo[3.2.1]Octane Derivative
Author(s) Deguin, B. ; Vogel, P.
Published in Tetrahedron Letters
Volume 34
Issue 39
Pages 6269-6270
Date 1993
ISSN 0040-4039
Keywords
Note Univ lausanne,chim sect,2 rue barre,ch-1005 lausanne,switzerland.
DOI https://doi.org/10.1016/S0040-4039(00)73728-2
Laboratories LGSA
Record Appears in Scientific production and competences > SB - School of Basic Sciences > SB Archives > LGSA - Laboratory of Glycochemistry and Asymmetric Synthesis
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date 2005-11-09

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