title: Dichotomy of Reductive Addition of Amines to Cyclopropyl Ketones vs Pyrrolidine Synthesis.
abstract: An interesting catalytic dichotomy was discovered: switching between simple ligand-free catalysts leads to fundamentally different outcomes of reductive reaction between amines and α-carbonylcyclopropanes. Whereas a rhodium catalyst leads to the traditional reductive amination product, ruthenium catalysis enables a novel reaction of pyrrolidine synthesis via ring expansion. The protocols do not require an external hydrogen source and employ carbon monoxide as a deoxygenative agent. The developed methodologies are perfectly compatible with a number of synthetically important functionalities such as ester, carboxyl, bromo, and Cbz moieties.
authors: A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences , Vavilova St 28, Moscow 119991, Russian Federation.
authors: Oleg I
authors: OI
authors: Afanasyev
authors: A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences , Vavilova St 28, Moscow 119991, Russian Federation.
authors: Alexey A
authors: AA
authors: Tsygankov
authors: A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences , Vavilova St 28, Moscow 119991, Russian Federation.
authors: Dmitry L
authors: DL
authors: Usanov
authors: A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences , Vavilova St 28, Moscow 119991, Russian Federation.|Department of Organic Chemistry, RUDN University , 6 Miklukho-Maklaya Street, Moscow 117198, Russia.
authors: Denis
authors: D
authors: Chusov