ja8b09251_si_001.cif (16.09 kB)
Copper(II)-Catalyzed Asymmetric Photoredox Reactions: Enantioselective Alkylation of Imines Driven by Visible Light
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posted on 2018-10-16, 00:00 authored by Yanjun Li, Kexu Zhou, Zhaorui Wen, Shi Cao, Xiang Shen, Meng Lei, Lei GongAsymmetric
photoredox catalysis offers exciting opportunities to
develop new synthetic approaches to chiral molecules through novel
reaction pathways. Employing the first-row transition metal complexes
as the chiral photoredox catalysts remains, however, a formidable
challenge, although these complexes are economic, environmentally
friendly, and often exhibit special reactivities. We report in this
Article the development of one class of highly efficient asymmetric/photoredox
bifunctional catalysts based on the copper(II) bisoxazoline complexes
(CuII–BOX) for the light-induced enantioselective
alkylation of imines. The reactions proceed under very mild conditions
and without a need for any other photosensitizer. The simple catalytic
system and readily tunable chiral ligands enable a significantly high
level of enantioselectivity for the formation of chiral amine products
bearing a tetrasubstituted carbon stereocenter (36 examples, up to
98% ee). Overall, the CuII–BOX catalysts initiate
the radical generation, and also govern the subsequent stereoselective
transformations. This strategy utilizing chiral complexes comprised
of a first-row transition metal and a flexible chiral ligand as the
asymmetric photoredox catalysts provides an effective platform for
the development of green asymmetric synthetic methods.
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Keywords
stereoselective transformationschiral amine productsfirst-row transition metallight-induced enantioselective alkylationVisible Light Asymmetric photoredox catalysisphotoredox catalystschiral moleculestunable chiral ligandschiral ligandchiral complexesIIchiral photoredox catalystsnovel reaction pathwaysfirst-row transition metal complexesEnantioselective Alkylation