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An Enantioselective Cp x Rh(III)‐Catalyzed C−H Functionalization/Ring‐Opening Route to Chiral Cyclopentenylamines
Author(s) -
Wang ShouGuo,
Cramer Nicolai
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201813953
Subject(s) - enantioselective synthesis , chemistry , catalysis , ring (chemistry) , peroxide , oxime , surface modification , aryl , medicinal chemistry , stereochemistry , organic chemistry , alkyl
A chiral Cp x Rh III catalyst system in situ generated from a Cp x Rh I (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.