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Modification of QuinoxP*-Type Bisphosphine Ligands for High-Performance Asymmetric Boryl Substitution of Racemic Allyl Electrophiles

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Copper(I)-Catalyzed Stereoselective Borylation Reactions

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Abstract

Optically active organoboron compounds are important building blocks in organic synthesis, especially α-chiral allylic boronates because various methods for enantiospecific derivatization of the boryl group have been developed and are now available. Here, I developed the new chiral bisphosphine ligands based on a non-covalent interaction strategy and improved the reactivity and enantioselectivity of copper(I)-catalyzed enantioselective borylation reactions, which provided cyclic and linear internal optically active allylic boronates from racemic allylic electrophiles. The product, allylic boronates, could be transformed into optically active homoallylic alcohols with high diastereoselectivity. Furthermore, the effect of non-covalent interaction in the ligands on reactivity and the origin of enantioselectivity are analyzed and discussed using state-of-the-art DFT calculations.

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  1. Synthetic Organic Chemistry Laboratories, FUJIFILM Corporation, Shizuoka, Japan

    Yu Ozawa

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Ozawa, Y. (2023). Modification of QuinoxP*-Type Bisphosphine Ligands for High-Performance Asymmetric Boryl Substitution of Racemic Allyl Electrophiles. In: Copper(I)-Catalyzed Stereoselective Borylation Reactions. Springer Theses. Springer, Singapore. https://doi.org/10.1007/978-981-99-1098-4_2

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