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Stereoselective Copper‐Catalyzed Intramolecular Alkene Aminooxygenation: Effects of Substrate and Ligand Structure on Selectivity
Author(s) -
Paderes Monissa C.,
Chemler Sherry R.
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100444
Subject(s) - chemistry , intramolecular force , alkene , enantioselective synthesis , substituent , selectivity , stereoselectivity , ligand (biochemistry) , catalysis , substrate (aquarium) , copper , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , receptor , oceanography , biochemistry , geology
A new protocol for diastereoselective copper‐catalyzed intramolecular alkene aminooxygenation, which provides methyleneoxy‐functionalized disubstituted pyrrolidines and five‐membered cyclic ureas from the corresponding γ‐alkenylsulfonamides and N ‐allylureas, is reported. In addition, some success was achieved in enantioselective desymmetrizations reactions. We discovered that the level of enantioselectivity and diastereoselectivity could be tuned by choice of copper(II) ligands and substrate N ‐substituent.