The low racemization barrier inherent in axially chiral vinyl sulfides/selenides (G ≤ 26.8 kcal/mol) poses a significant challenge for achieving atroposelective hydrochalcogenation of alkynes. In this study, we present an unprecedented atroposelective hydrochalcogenation of alkynes catalyzed by organocatalysts. This organocatalytic, atom-economic process proceeds under mild conditions and exhibits exceptional enantio-, regio-, and E-stereoselectivity. Insights from detailed Density Functional Theory (DFT) studies elucidate the origins of these high selectivities.
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Wang et al. (2024) studied this question.
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