An Asymmetric Ortholithiation Approach to Inherently Chiral Calix[4]arenes
Organic Letters2009Vol. 11(21), pp. 4986–4989
Citations Over TimeTop 12% of 2009 papers
Abstract
A general asymmetric synthesis of inherently chiral calix[4]arenes is described: using a chiral oxazoline derived from L-valine, an ortholithiation strategy is employed to give inherently chiral calix[4]arenes with high (93%) enantiomeric excesses. A crystal structure of a phosphine oxide intermediate has been obtained, unambiguously assigning the major diastereomer in the reaction; a mechanism explaining this result is proposed.
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