Enantioselective Cpx RhIII -Catalyzed Carboaminations of Acrylates.
Angew Chem Int Ed Engl. 2020 08 10; 59(33):14129-14133.AC

Abstract

Enantioselective carboaminations of olefins constitute an attractive strategy for a rapid increase in molecular complexity from readily available starting materials. Reported here is an intermolecular asymmetric carboamination of acrylates using rhodium(III)-catalyzed alkenyl C-H activations of N-enoxysuccinimides to generate the nitrogen and carbon portion for the transfer. A rhodium complex equipped with a tailored bulky trisubstituted chiral Cpx ligand ensures carboamination chemoselectivity as well high levels of enantioinduction. The transformation operates under mild reaction conditions at ambient temperatures and provides access to a variety of α-amino esters in good yields and excellent enantiomeric ratios of >99.5:0.5.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Duchemin C

Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), Lausanne, Switzerland.

Cramer N

Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), Lausanne, Switzerland.

Pub Type(s)

Journal Article

Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

32410313

Citation

Duchemin, Coralie, and Nicolai Cramer. "Enantioselective Cpx RhIII -Catalyzed Carboaminations of Acrylates." Angewandte Chemie (International Ed. in English), vol. 59, no. 33, 2020, pp. 14129-14133.

Duchemin C, Cramer N. Enantioselective Cpx RhIII -Catalyzed Carboaminations of Acrylates. Angew Chem Int Ed Engl. 2020;59(33):14129-14133.

Duchemin, C., & Cramer, N. (2020). Enantioselective Cpx RhIII -Catalyzed Carboaminations of Acrylates. Angewandte Chemie (International Ed. in English), 59(33), 14129-14133. https://doi.org/10.1002/anie.202006149

Duchemin C, Cramer N. Enantioselective Cpx RhIII -Catalyzed Carboaminations of Acrylates. Angew Chem Int Ed Engl. 2020 08 10;59(33):14129-14133. PubMed PMID: 32410313.

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

TY - JOUR T1 - Enantioselective Cpx RhIII -Catalyzed Carboaminations of Acrylates. AU - Duchemin,Coralie, AU - Cramer,Nicolai, Y1 - 2020/06/09/ PY - 2020/04/28/received PY - 2020/5/16/pubmed PY - 2020/5/16/medline PY - 2020/5/16/entrez KW - C−H activation KW - asymmetric catalysis KW - carboamination KW - cyclopentadienyl ligands KW - rhodium SP - 14129 EP - 14133 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 59 IS - 33 N2 - Enantioselective carboaminations of olefins constitute an attractive strategy for a rapid increase in molecular complexity from readily available starting materials. Reported here is an intermolecular asymmetric carboamination of acrylates using rhodium(III)-catalyzed alkenyl C-H activations of N-enoxysuccinimides to generate the nitrogen and carbon portion for the transfer. A rhodium complex equipped with a tailored bulky trisubstituted chiral Cpx ligand ensures carboamination chemoselectivity as well high levels of enantioinduction. The transformation operates under mild reaction conditions at ambient temperatures and provides access to a variety of α-amino esters in good yields and excellent enantiomeric ratios of >99.5:0.5. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/32410313/Enantioselective_Cpx_RhIII__Catalyzed_Carboaminations_of_Acrylates_ DB - PRIME DP - Unbound Medicine ER -

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Enantioselective Cpx RhIII -Catalyzed Carboaminations of Acrylates.Angew Chem Int Ed Engl. 2020 08 10; 59(33):14129-14133.AC