Synthesis and Lewis acid assisted rearrangement of novel donor-acceptor substituted cyclopropanes: highly stereoselective [4+1] annulation approach to substituted and spiro cyclopentene derivatives

Satyanarayana, Janagani ; Rao, Mandava V. Basaveswara ; Ila, Hiriyakkanavar ; Junjappa, Hiriyakkanavar (1996) Synthesis and Lewis acid assisted rearrangement of novel donor-acceptor substituted cyclopropanes: highly stereoselective [4+1] annulation approach to substituted and spiro cyclopentene derivatives Tetrahedron Letters, 37 (20). pp. 3565-3568. ISSN 0040-4039

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/004040...

Related URL: http://dx.doi.org/10.1016/0040-4039(96)00622-3

Abstract

The cyclopropanes 2a-h having 4-(bismethylthio)butadienyl moiety as donor group, which are easily obtained by regioselective cyclopropanation of vinylogous ketene dithioacetals 1a-h with oxodimethylsulphonium methylide, undergo facile Lewis acid assisted vinylcyclopropyl rearrangement to afford substituted and spiro cyclopentenes 3a-h in good yields.

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