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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 (CC BY 3.0).
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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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