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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.
Molecules. 2012 Dec 20; 18(1):14-26.M

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.

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Authors+Show Affiliations

Yamamoto Y
Frontier Chemistry Center, Hokkaido University, Sapporo, Japan. yasuyama@eng.hokudai.ac.jp
Kurihara K
No affiliation info available
Takahashi Y
No affiliation info available
Miyaura N
No affiliation info available

MeSH

Boronic AcidsCatalysisKetonesLigandsMagnetic Resonance SpectroscopyMolecular StructureOrganophosphorus CompoundsRhodium

Pub Type(s)

Journal Article

Language

eng

PubMed ID

23344185

Citation

Yamamoto, Yasunori, et al. "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 (Basel, Switzerland), vol. 18, no. 1, 2012, pp. 14-26.
Yamamoto Y, Kurihara K, Takahashi Y, et al. 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. 2012;18(1):14-26.
Yamamoto, Y., Kurihara, K., Takahashi, Y., & Miyaura, N. (2012). 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 (Basel, Switzerland), 18(1), 14-26. https://doi.org/10.3390/molecules18010014
Yamamoto Y, et al. 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. 2012 Dec 20;18(1):14-26. PubMed PMID: 23344185.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - An N-linked bidentate phosphoramidite ligand (N-Me-BIPAM) for rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones. AU - Yamamoto,Yasunori, AU - Kurihara,Kazunori, AU - Takahashi,Yoshinori, AU - Miyaura,Norio, Y1 - 2012/12/20/ PY - 2012/11/30/received PY - 2012/12/14/revised PY - 2012/12/17/accepted PY - 2013/1/25/entrez PY - 2013/1/25/pubmed PY - 2013/6/12/medline SP - 14 EP - 26 JF - Molecules (Basel, Switzerland) JO - Molecules VL - 18 IS - 1 N2 - 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. SN - 1420-3049 UR - https://www.unboundmedicine.com/medline/citation/23344185/An_N_linked_bidentate_phosphoramidite_ligand__N_Me_BIPAM__for_rhodium_catalyzed_asymmetric_14_addition_of_arylboronic_acids_to_αβ_unsaturated_ketones_ L2 - https://www.mdpi.com/resolver?pii=molecules18010014 DB - PRIME DP - Unbound Medicine ER -