American Chemical Society
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α‑Ketophosphonates as Ester Surrogates: Isothiourea-Catalyzed Asymmetric Diester and Lactone Synthesis

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posted on 2014-05-02, 00:00 authored by Siobhan R. Smith, Stuart M. Leckie, Reuben Holmes, James Douglas, Charlene Fallan, Peter Shapland, David Pryde, Alexandra M. Z. Slawin, Andrew D. Smith
Isothiourea HBTM-2.1 catalyzes the asymmetric Michael addition/lactonization of aryl- and alkenylacetic acids using α-keto-β,γ-unsaturated phosphonates as α,β-unsaturated ester surrogates, giving access to a diverse range of stereodefined lactones or enantioenriched functionalized diesters upon ring-opening.