Copper(II)-Catalyzed Transannular Enantioselective Intramolecular Carboamination of Alkenes
Hosseini, Azade S.
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Carboamination is the formation of a C-C and a C-N bond across an alkene. This is an attractive method to form nitrogen heterocycles, which are found in many biologically relevant molecules and natural product targets. Using a Copper(II)-complex to catalyze a transannular enantioselective alkene carboamination, we can form 3-benzazepine compounds with great yields and high enantioselectivity. Our proposed syn-aminocupration transition state demonstrates that the use of a chiral ligand will set the stereochemistry of our product in this step. Using a general substrate, we have been able to lower the catalyst loading, time and temperature of these reactions to produce a transannular intramolecular carboamination product with comparable yields and high enantioselectivty. More recently, we have expanded our substrate scope to include compounds with substitution at the para-position of the phenyl ring. We have also included substrates that introduce substituted alkenes and with both cases, we have been able to reproduce high yields and achieve enantioselectivity. In the future, we hope to include various ortho and meta-subsituted compounds into our substrate scope to observe how this will affect the selectivity of our product. We would also like to include substrates with heterocycles, where we introduce sulfur and oxygen atoms into the ring.