Wittig rearrangements ([2,3]- and [1,2]) of α-allyloxy carbanion is an excellent method for regio- and stereoselective formation of C-C bond but often produces mixtures of both products via competing reaction pathways (Figure-1). We developed a removable functional group strategy to achieve reversibility to control the kinetic vs thermodynamic Wittig products for its regiodivergency.2 With the α-propargyl carbanion system, we observed an unprecedented anionic endo-dig cyclization product, which further complicates the product selectivity. Although this carbanion cyclization is not reported, an aborted carbanionic endo-dig cyclization via common transition state for [2,3] rearrangement is proposed computationally.1 We establish a reaction condition to achieve the cyclization product selectively for wide range of substrate class.

An Approach for Metal Free Carbanion Endo-dig Cyclization via Reversibility of [2,3]-Wittig Rearrangement

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27th CRSI National Symposium in Chemistry

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