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Molecules 2013, 18(1), 14-26; doi:10.3390/molecules18010014
Article

An N-Linked Bidentate Phosphoramidite Ligand (N-Me-BIPAM) for Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Ketones

* , ,  and
Frontier Chemistry Center, Faculty of Engineering, Hokkaido University, Sapporo 060-8628, Japan
* Author to whom correspondence should be addressed.
Received: 30 November 2012 / Revised: 14 December 2012 / Accepted: 17 December 2012 / Published: 20 December 2012
(This article belongs to the Special Issue Organoboron Chemistry)
Download PDF [354 KB, 18 June 2014; original version 18 June 2014]

Abstract

A new bidentate phosphoramidite (N-Me-BIPAM) based on Shibasaki’s N-linked BINOL was synthesized. This ligand appears to be highly effective for rhodium-catalyzed asymmetric conjugated addition of arylboronic acids to α,β-unsaturated enones. The reaction of ortho-substituted arylboronic acid with acyclic and cyclic enones provides the corresponding products in good yields and enantioselectivities.
Keywords: asymmetric conjugate addition; rhodium catalyst; bidentate phosphoramidite ligand asymmetric conjugate addition; rhodium catalyst; bidentate phosphoramidite ligand
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Yamamoto, Y.; Kurihara, K.; Takahashi, Y.; Miyaura, N. An N-Linked Bidentate Phosphoramidite Ligand (N-Me-BIPAM) for Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Ketones. Molecules 2013, 18, 14-26.

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