ArticleScience advances2025
Noncovalent interaction-driven regio- and enantioselective hydroalkynylation of unactivated alkenes to access remote chiral nitriles.
Article in Science advances, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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6 authors.
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Abstract
Unactivated alkenes represent a challenging substrate for selective functionalization, particularly in achieving both regioselectivity and enantioselectivity. In this study, we present a strategy for the regio- and enantioselective hydroalkynylation of unactivated alkenes through the integration of noncovalent π⋯π interactions between the cyano group of the substrate and a chiral bis(oxazoline) ligand. The weak π⋯π interaction was supported by control experiments and computational studies. The method provides a reliable approach for synthesizing chiral nitriles with remote (β-, γ-, and δ-) stereocenters, which exhibit orthogonal reactivities and serve as valuable intermediates for further derivatization into otherwise difficult-to-access compounds. Our work provides a strategy for olefin functionalization and opens up avenues for the selective synthesis of chiral nitriles with remote stereocenters.
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