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Stereoselective and Regioselective Synthesis of Heterocycles via Copper-Catalyzed Additions of Amine Derivatives and Alcohols to Alkenes

Author:
Chemler, Sherry R., Karyakarte, Shuklendu D., Khoder, Zainab M.
Source:
Journal of organic chemistry 2017 v.82 no.21 pp. 11311-11325
ISSN:
1520-6904
Subject:
alcohols, alkenes, amination, chemical structure, copper, energy, nitrogen, organic chemistry, oxygen, reaction mechanisms, regioselectivity, stereoselectivity
Abstract:
This Perspective describes the development of a family of copper(II)-catalyzed alkene difunctionalization reactions that enable stereoselective addition of amine derivatives and alcohols onto pendant unactivated alkenes to provide a range of valuable saturated nitrogen and oxygen heterocycles. 2-Vinylanilines and related substrates undergo alternative oxidative amination or allylic amination pathways, and these reactions will also be discussed. The involvement of both polar and radical steps in the reaction mechanisms have been implicated. Major product formation is a function of the lowest energy pathway, which in turn is a function of structural aspects of the various reaction components.
Agid:
5851214