Chiral Cp-rhodium(III)-catalyzed asymmetric hydroarylations of 1,1-disubstituted alkenes.
Angew Chem Int Ed Engl. 2014 Jan 07; 53(2):507-11.AC

Abstract

Metal-catalyzed functionalizations at the ortho position of a directing group have become an efficient bond-forming strategy. A wide range of transformations that employ Cp*Rh(III) catalysts have been described, but despite their synthetic potential, enantioselective variants that use chiral versions of the Cp* ligand remain scarce (Cp*=pentamethyl cyclopentadienyl). Cyclopentadienyl compounds with an atropchiral biaryl backbone are shown to be suitable ligands for the efficient intramolecular enantioselective hydroarylation of aryl hydroxamates. Dihydrofurans that bear methyl-substituted quaternary stereocenters are thus obtained by CH functionalization under mild conditions.

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Authors+Show Affiliations

Ye B

Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, CH-1015 Lausanne (Switzerland) http://isic.epfl.ch/lcsa.

Donets PA

No affiliation info available

Cramer N

No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

24311026

Citation

Ye, Baihua, et al. "Chiral Cp-rhodium(III)-catalyzed Asymmetric Hydroarylations of 1,1-disubstituted Alkenes." Angewandte Chemie (International Ed. in English), vol. 53, no. 2, 2014, pp. 507-11.

Ye B, Donets PA, Cramer N. Chiral Cp-rhodium(III)-catalyzed asymmetric hydroarylations of 1,1-disubstituted alkenes. Angew Chem Int Ed Engl. 2014;53(2):507-11.

Ye, B., Donets, P. A., & Cramer, N. (2014). Chiral Cp-rhodium(III)-catalyzed asymmetric hydroarylations of 1,1-disubstituted alkenes. Angewandte Chemie (International Ed. in English), 53(2), 507-11. https://doi.org/10.1002/anie.201309207

Ye B, Donets PA, Cramer N. Chiral Cp-rhodium(III)-catalyzed Asymmetric Hydroarylations of 1,1-disubstituted Alkenes. Angew Chem Int Ed Engl. 2014 Jan 7;53(2):507-11. PubMed PMID: 24311026.

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

TY - JOUR T1 - Chiral Cp-rhodium(III)-catalyzed asymmetric hydroarylations of 1,1-disubstituted alkenes. AU - Ye,Baihua, AU - Donets,Pavel A, AU - Cramer,Nicolai, Y1 - 2013/12/06/ PY - 2013/10/22/received PY - 2013/12/7/entrez PY - 2013/12/7/pubmed PY - 2013/12/7/medline KW - CH activation KW - asymmetric catalysis KW - cyclopentadienyl ligands KW - hydroarylation KW - rhodium SP - 507 EP - 11 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 53 IS - 2 N2 - Metal-catalyzed functionalizations at the ortho position of a directing group have become an efficient bond-forming strategy. A wide range of transformations that employ Cp*Rh(III) catalysts have been described, but despite their synthetic potential, enantioselective variants that use chiral versions of the Cp* ligand remain scarce (Cp*=pentamethyl cyclopentadienyl). Cyclopentadienyl compounds with an atropchiral biaryl backbone are shown to be suitable ligands for the efficient intramolecular enantioselective hydroarylation of aryl hydroxamates. Dihydrofurans that bear methyl-substituted quaternary stereocenters are thus obtained by CH functionalization under mild conditions. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/24311026/Chiral_Cp_rhodium_III__catalyzed_asymmetric_hydroarylations_of_11_disubstituted_alkenes_ DB - PRIME DP - Unbound Medicine ER -

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Chiral Cp-rhodium(III)-catalyzed asymmetric hydroarylations of 1,1-disubstituted alkenes.Angew Chem Int Ed Engl. 2014 Jan 07; 53(2):507-11.AC