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.
Links
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 -