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Nishimura T, Noishiki A, Tsui GC, et al. Asymmetric synthesis of (triaryl)methylamines by rhodium-catalyzed addition of arylboroxines to cyclic N-sulfonyl ketimines. J Am Chem Soc. 2012;134(11):5056-9doi: 10.1021/ja300697c.
Nishimura, T., Noishiki, A., Tsui, G. C., & Hayashi, T. (2012). Asymmetric synthesis of (triaryl)methylamines by rhodium-catalyzed addition of arylboroxines to cyclic N-sulfonyl ketimines. Journal of the American Chemical Society, 134(11), 5056-9. https://doi.org/10.1021/ja300697c
Nishimura, Takahiro, et al. "Asymmetric synthesis of (triaryl)methylamines by rhodium-catalyzed addition of arylboroxines to cyclic N-sulfonyl ketimines." Journal of the American Chemical Society vol. 134,11 (2012): 5056-9. doi: https://doi.org/10.1021/ja300697c
Nishimura T, Noishiki A, Tsui GC, Hayashi T. Asymmetric synthesis of (triaryl)methylamines by rhodium-catalyzed addition of arylboroxines to cyclic N-sulfonyl ketimines. J Am Chem Soc. 2012 Mar 21;134(11):5056-9. doi: 10.1021/ja300697c. Epub 2012 Mar 08. PMID: 22394013.
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J Am Chem Soc. 2012 Mar 21;134(11):5056-9. doi: 10.1021/ja300697c. Epub 2012 Mar 08.

Asymmetric synthesis of (triaryl)methylamines by rhodium-catalyzed addition of arylboroxines to cyclic N-sulfonyl ketimines.

Journal of the American Chemical Society

Takahiro Nishimura, Akira Noishiki, Gavin Chit Tsui, Tamio Hayashi

Affiliations

  1. Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan. [email protected]

PMID: 22394013 DOI: 10.1021/ja300697c

Abstract

Asymmetric addition of arylboroxines to cyclic N-sulfonyl ketimines proceeded in the presence of a rhodium catalyst coordinated with a chiral diene ligand to give high yields of benzosultams, where a triaryl-substituted stereogenic carbon center was created with high enantioselectivity (93-99% ee). The chiral benzosultams were transformed into the chiral (triaryl)methylamines by breaking the cyclic structure.

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