An Enantioselective Cp^xRh(III)‐Catalyzed C−H Functionalization/Ring‐Opening Route to Chiral Cyclopentenylamines Article Swipe

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Enantioselective synthesis Catalysis Chemistry Ring (chemistry) Peroxide Oxime Surface modification Medicinal chemistry Aryl Stereochemistry Combinatorial chemistry Organic chemistry Alkyl Physical chemistry

Shouguo Wang , Nicolai Cramer ·

YOU? · · 2019 · Open Access · · DOI: https://doi.org/10.1002/anie.201813953 · OA: W2907960580

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.