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

doi:10.3390/molecules18010014

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

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

Yasunori Yamamoto* , Kazunori Kurihara, Yoshinori Takahashi and Norio Miyaura

Frontier Chemistry Center, Faculty of Engineering, Hokkaido University, Sapporo 060-8628, Japan

* Author to whom correspondence should be addressed.

Received: 30 November 2012; in revised form: 14 December 2012 / Accepted: 17 December 2012 / Published: 20 December 2012

(This article belongs to the Special Issue Organoboron Chemistry)

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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

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MDPI and ACS Style

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.

AMA Style

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(1):14-26.

Chicago/Turabian Style

Yamamoto, Yasunori; Kurihara, Kazunori; Takahashi, Yoshinori; Miyaura, Norio. 2013. "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 18, no. 1: 14-26.

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