A tunable class of chiral Cp ligands for enantioselective rhodium(III)-catalyzed C-H allylations of benzamides.
J Am Chem Soc. 2013 Jan 16; 135(2):636-9.JA

Abstract

The lack of robust and tunable chiral versions of cyclopentadienyl (Cp) ligands hampers progress in the development of catalytic asymmetric versions of a myriad of reactions catalyzed by this ubiquitous ligand. Herein, we describe of a class of chiral Cp ligands with tunable steric parameters. Coordinated to transition metals, the ligand creates a well-defined chiral pocket, able to imprint its chirality onto the metal. The corresponding Rh complexes are shown to be excellent catalysts for enantioselective allylation of N-methoxybenzamides via directed C-H functionalizations at very mild conditions. The obtained enantioselectivities are excellent and demonstrate the viability of chiral Cp complexes as selective transition metal catalysts.

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Authors+Show Affiliations

Ye B

Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, Lausanne CH-1015, Switzerland.

Cramer N

No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

23286204

Citation

Ye, Baihua, and Nicolai Cramer. "A Tunable Class of Chiral Cp Ligands for Enantioselective rhodium(III)-catalyzed C-H Allylations of Benzamides." Journal of the American Chemical Society, vol. 135, no. 2, 2013, pp. 636-9.

Ye B, Cramer N. A tunable class of chiral Cp ligands for enantioselective rhodium(III)-catalyzed C-H allylations of benzamides. J Am Chem Soc. 2013;135(2):636-9.

Ye, B., & Cramer, N. (2013). A tunable class of chiral Cp ligands for enantioselective rhodium(III)-catalyzed C-H allylations of benzamides. Journal of the American Chemical Society, 135(2), 636-9. https://doi.org/10.1021/ja311956k

Ye B, Cramer N. A Tunable Class of Chiral Cp Ligands for Enantioselective rhodium(III)-catalyzed C-H Allylations of Benzamides. J Am Chem Soc. 2013 Jan 16;135(2):636-9. PubMed PMID: 23286204.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - A tunable class of chiral Cp ligands for enantioselective rhodium(III)-catalyzed C-H allylations of benzamides. AU - Ye,Baihua, AU - Cramer,Nicolai, Y1 - 2013/01/07/ PY - 2013/1/5/entrez PY - 2013/1/5/pubmed PY - 2013/1/5/medline SP - 636 EP - 9 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 135 IS - 2 N2 - The lack of robust and tunable chiral versions of cyclopentadienyl (Cp) ligands hampers progress in the development of catalytic asymmetric versions of a myriad of reactions catalyzed by this ubiquitous ligand. Herein, we describe of a class of chiral Cp ligands with tunable steric parameters. Coordinated to transition metals, the ligand creates a well-defined chiral pocket, able to imprint its chirality onto the metal. The corresponding Rh complexes are shown to be excellent catalysts for enantioselective allylation of N-methoxybenzamides via directed C-H functionalizations at very mild conditions. The obtained enantioselectivities are excellent and demonstrate the viability of chiral Cp complexes as selective transition metal catalysts. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/23286204/A_tunable_class_of_chiral_Cp_ligands_for_enantioselective_rhodium_III__catalyzed_C_H_allylations_of_benzamides_ L2 - https://doi.org/10.1021/ja311956k DB - PRIME DP - Unbound Medicine ER -

Tags

A tunable class of chiral Cp ligands for enantioselective rhodium(III)-catalyzed C-H allylations of benzamides.J Am Chem Soc. 2013 Jan 16; 135(2):636-9.JA