Unexpected cis-Selectivity in (Sylvestre) Julia Olefinations with Bu3Sn-Containing Allyl Benzothiazolyl Sulfones: Stereoselective Synthesis of 1,3-Butadienyl- and 1,3,5-Hexatrienylstannanes

Unexpected cis-Selectivity in (Sylvestre) Julia Olefinations with Bu3Sn-Containing Allyl Benzothiazolyl Sulfones: Stereoselective Synthesis of 1,3-Butadienyl- and 1,3,5-Hexatrienylstannanes

Abstract Bu 3 Sn-substituted benzothiazolyl sulfones 1C, 1D, and 1F were subjected to Julia olefination reactions with a variety of aldehydes. CIS-Selectivities up to 97:3 were obtained by using KHMDS as base in THF.

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Veröffentlicht in:Synlett 2005-02, Vol.2005 (2), p.289-293
Hauptverfasser: Sorg, Achim, Brückner, Reinhard
Format: Artikel
Sprache:eng
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Zusammenfassung:Abstract Bu 3 Sn-substituted benzothiazolyl sulfones 1C, 1D, and 1F were subjected to Julia olefination reactions with a variety of aldehydes. CIS-Selectivities up to 97:3 were obtained by using KHMDS as base in THF.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2004-837213