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Access to P- and Axially Chiral Biaryl Phosphine Oxides by Enantioselective Cpx IrIII -Catalyzed C-H Arylations.
Angew Chem Int Ed Engl. 2018 Sep 24; 57(39):12901-12905.AC

Abstract

An enantioselective C-H arylation of phosphine oxides with o-quinone diazides catalyzed by an iridium(III) complex bearing an atropchiral cyclopentadienyl (Cpx) ligand and phthaloyl tert-leucine as co-catalyst is reported. The method allows access to a) P-chiral biaryl phosphine oxides, b) atropo-enantioselective construction of sterically demanding biaryl backbones, and also c) selective assembly of axial and P-chiral compounds in excellent yields and diastereo- and enantioselectivities. Enantiospecific reductions provide monodentate chiral phosphorus(III) compounds having structures and biaryl backbones with proven importance as ligands in asymmetric catalysis.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Jang YS
Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, CH-, 1015, Lausanne, Switzerland.
Woźniak Ł
Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, CH-, 1015, Lausanne, Switzerland.
Pedroni J
Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, CH-, 1015, Lausanne, Switzerland.
Cramer N
Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, CH-, 1015, Lausanne, Switzerland.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

30044513

Citation

Jang, Yun-Suk, et al. "Access to P- and Axially Chiral Biaryl Phosphine Oxides By Enantioselective Cpx IrIII -Catalyzed C-H Arylations." Angewandte Chemie (International Ed. in English), vol. 57, no. 39, 2018, pp. 12901-12905.
Jang YS, Woźniak Ł, Pedroni J, et al. Access to P- and Axially Chiral Biaryl Phosphine Oxides by Enantioselective Cpx IrIII -Catalyzed C-H Arylations. Angew Chem Int Ed Engl. 2018;57(39):12901-12905.
Jang, Y. S., Woźniak, Ł., Pedroni, J., & Cramer, N. (2018). Access to P- and Axially Chiral Biaryl Phosphine Oxides by Enantioselective Cpx IrIII -Catalyzed C-H Arylations. Angewandte Chemie (International Ed. in English), 57(39), 12901-12905. https://doi.org/10.1002/anie.201807749
Jang YS, et al. Access to P- and Axially Chiral Biaryl Phosphine Oxides By Enantioselective Cpx IrIII -Catalyzed C-H Arylations. Angew Chem Int Ed Engl. 2018 Sep 24;57(39):12901-12905. PubMed PMID: 30044513.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Access to P- and Axially Chiral Biaryl Phosphine Oxides by Enantioselective Cpx IrIII -Catalyzed C-H Arylations. AU - Jang,Yun-Suk, AU - Woźniak,Łukasz, AU - Pedroni,Julia, AU - Cramer,Nicolai, Y1 - 2018/08/29/ PY - 2018/07/06/received PY - 2018/7/26/pubmed PY - 2018/7/26/medline PY - 2018/7/26/entrez KW - C−H activation KW - P-chirality KW - asymmetric catalysis KW - chiral Cp ligands KW - iridium SP - 12901 EP - 12905 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 57 IS - 39 N2 - An enantioselective C-H arylation of phosphine oxides with o-quinone diazides catalyzed by an iridium(III) complex bearing an atropchiral cyclopentadienyl (Cpx) ligand and phthaloyl tert-leucine as co-catalyst is reported. The method allows access to a) P-chiral biaryl phosphine oxides, b) atropo-enantioselective construction of sterically demanding biaryl backbones, and also c) selective assembly of axial and P-chiral compounds in excellent yields and diastereo- and enantioselectivities. Enantiospecific reductions provide monodentate chiral phosphorus(III) compounds having structures and biaryl backbones with proven importance as ligands in asymmetric catalysis. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/30044513/Access_to_P__and_Axially_Chiral_Biaryl_Phosphine_Oxides_by_Enantioselective_Cpx_IrIII__Catalyzed_C_H_Arylations_ DB - PRIME DP - Unbound Medicine ER -