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An Enantioselective Cpx Rh(III)-Catalyzed C-H Functionalization/Ring-Opening Route to Chiral Cyclopentenylamines.
Angew Chem Int Ed Engl. 2019 Feb 18; 58(8):2514-2518.AC

Abstract

A chiral Cpx RhIII catalyst system in situ generated from a Cpx RhI (cod) precatalyst and bis(o-toluoyl) peroxide as activating oxidant was developed for a C-H activation/ring-opening sequence between aryl ketoxime ethers and 2,3-diazabicyclo[2.2.1]hept-5-enes. This transformation provides access to densely functionalized chiral cyclopentenylamines in excellent yields and enantioselectivities of up to 97:3 er. The reported method is also well suitable for asymmetric alkenyl C-H functionalizations of α,β-unsaturated oxime ethers, furnishing skipped dienes with high levels of enantiocontrol.

Authors+Show Affiliations

Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, 1015, Lausanne, Switzerland.Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, 1015, Lausanne, Switzerland.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

30600903

Citation

Wang, Shou-Guo, and Nicolai Cramer. "An Enantioselective Cpx Rh(III)-Catalyzed C-H Functionalization/Ring-Opening Route to Chiral Cyclopentenylamines." Angewandte Chemie (International Ed. in English), vol. 58, no. 8, 2019, pp. 2514-2518.
Wang SG, Cramer N. An Enantioselective Cpx Rh(III)-Catalyzed C-H Functionalization/Ring-Opening Route to Chiral Cyclopentenylamines. Angew Chem Int Ed Engl. 2019;58(8):2514-2518.
Wang, S. G., & Cramer, N. (2019). An Enantioselective Cpx Rh(III)-Catalyzed C-H Functionalization/Ring-Opening Route to Chiral Cyclopentenylamines. Angewandte Chemie (International Ed. in English), 58(8), 2514-2518. https://doi.org/10.1002/anie.201813953
Wang SG, Cramer N. An Enantioselective Cpx Rh(III)-Catalyzed C-H Functionalization/Ring-Opening Route to Chiral Cyclopentenylamines. Angew Chem Int Ed Engl. 2019 Feb 18;58(8):2514-2518. PubMed PMID: 30600903.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - An Enantioselective Cpx Rh(III)-Catalyzed C-H Functionalization/Ring-Opening Route to Chiral Cyclopentenylamines. AU - Wang,Shou-Guo, AU - Cramer,Nicolai, Y1 - 2019/01/25/ PY - 2018/12/07/received PY - 2019/1/3/pubmed PY - 2019/1/3/medline PY - 2019/1/3/entrez KW - C−H activation KW - asymmetric catalysis KW - chiral Cp ligands KW - rhodium KW - ring opening SP - 2514 EP - 2518 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 58 IS - 8 N2 - A chiral Cpx RhIII catalyst system in situ generated from a Cpx RhI (cod) precatalyst and bis(o-toluoyl) peroxide as activating oxidant was developed for a C-H activation/ring-opening sequence between aryl ketoxime ethers and 2,3-diazabicyclo[2.2.1]hept-5-enes. This transformation provides access to densely functionalized chiral cyclopentenylamines in excellent yields and enantioselectivities of up to 97:3 er. The reported method is also well suitable for asymmetric alkenyl C-H functionalizations of α,β-unsaturated oxime ethers, furnishing skipped dienes with high levels of enantiocontrol. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/30600903/An_Enantioselective_Cpx_Rh_III__Catalyzed_C_H_Functionalization/Ring_Opening_Route_to_Chiral_Cyclopentenylamines_ DB - PRIME DP - Unbound Medicine ER -
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