Regio- and stereocontrolled preparation of alpha-substituted phosphonocrotonate derivatives

Solberghe, Geoffrey;Marko, Istvan
(2002) Tetrahedron Letters — Vol. 43, n° 29, p. 5061-5065 (2002)

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  • Solberghe, GeoffreyUCLouvain
    Author
  • Marko, IstvanUCLouvain
    Author
Abstract
Under suitable reaction conditions, monoalkylation of triethyl phosphonocrotonate 11 could be efficiently accomplished, leading to the preparation of a-substituted phosphonates 15. The reaction is totally regioselective and completely (E)-selective. The novel phosphonocrotonate 19 underwent smooth Horner-Emmons condensation, producing a key-precursor for the synthesis of the middle core of the manzamine alkaloids. (C) 2002 Elsevier Science Ltd. All rights reserved.
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Solberghe, G., & Marko, I. (2002). Regio- and stereocontrolled preparation of alpha-substituted phosphonocrotonate derivatives. Tetrahedron Letters, 43(29), 5061-5065. https://doi.org/10.1016/S0040-4039(02)01001-8 (Original work published 2002)