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Tandem Wittig Reaction-Ring Contraction of Cyclobutanes: A Route to Functionalized Cyclopropanecarbaldehydes

Federico Cuccu, Lorenzo Serusi, Alberto Luridiana, Francesco Secci, Pierluigi Caboni, David J. Aitken and Angelo Frongia*

*Dipartimento di Scienze Chimiche e Geologiche, UniversitÓ degli Studi di Cagliari, Complesso Universitario di Monserrato, S.S. 554, Bivio per Sestu, I-09042 Monserrato, Cagliari, Italy, Email: afrongiaunica.it

F. Cuccu, L. Serusi, A. Luridiana, F. Secci, P. Caboni, D. J. Aitken, A. Frongia, Org. Lett., 2019, 21, 7755-7758.

DOI: 10.1021/acs.orglett.9b02690 (free Supporting Information)



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Abstract

A tandem reaction consisting of a Wittig reaction-ring contraction process between α-hydroxycyclobutanone and phosphonium ylides provides highly functionalized cyclopropanecarbaldehydes in very good yield.

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proposed reaction pathway



Key Words

cyclopropanes, 1,4-diketones, Wittig reaction


ID: J54-Y2019