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Planar-Chiral Phosphine-Olefin Ligands Exploiting a (Cyclopentadienyl)manganese(I) Scaffold To Achieve High Robustness and High Enantioselectivity

Ken Kamikawa* , Ya-Yi Tseng, Jia-Hong Jian, Tamotsu Takahashi and Masamichi Ogasawara*

*Department of Chemistry, Osaka Prefecture University, Sakai, Osaka 599-8531; Department of Natural Science, Tokushima University, Tokushima 770-8506, Japan, Email: kamikawac.s.osakafu-u.ac.jp, ogasawartokushima-u.ac.jp

K. Kamikawa, Y.-Y. Tseng, J.-H. Jian, T. Takahashi, M. Ogasawara, J. Am. Chem. Soc., 2017, 139, 1545-1553.

DOI: 10.1021/jacs.6b11243


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Abstract

2-methyl-1,3-propenylene-bridged (η5-diarylphosphinocyclopentadienyl)(phosphine)manganese(I) dicarbonyl complexes show better robustness as well as higher enantioselectivity over phosphine-olefin ligands with a planar-chiral (η6-arene)chromium(0) framework in rhodium-catalyzed 1,4-additions of arylboronic acids to various cyclic/acyclic enones and asymmetric 1,2-additions of arylboron nucleophiles to imines or aldehydes.

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Key Words

1,4-addition


ID: J48-Y2017