The computer-assisted design of a new reaction is the most challenging subject, but the combination of recent improvement of the accuracy of calculations and iteration of DFT calculations and experimental evaluation enables the optimization of a highly selective catalyst. We developed a three-hindered-quadrant P-chirogenic bisphosphine ligand, which allowed the Markovnikov hydroboration to proceed with high enantioselectivity (Ito et al., Nature Comm. 2018, 9, 2290). The ligands are created by computer-assisted design with DFT calculations. The optimized bisphosphine ligand (S)-Quinox-tOctAd2 exhibited a broad substrate scope for terminal aliphatic alkenes and good functional-group tolerance to give various secondary chiral alkyl boronates with high regio- and enantioselectivity (branch/linear = 92:8, 99% ee).

Computer-assisted design of asymmetric copper-catalyzed borylation of terminal aliphatic alkenes

2019 Fall National Meeting

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