A Chiral Amine Transfer Approach to the Photocatalytic Asymmetric Synthesis of α-Trialkyl-α-tertiary Amines.


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Type
Article
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Authors
Trowbridge, Aaron D 
Abstract

A long-standing challenge within radical chemistry is that of controlling the absolute stereochemistry of the products. Here, we report the stereocontrolled addition of α-amino radicals reductively generated from imines via visible-light-mediated photoredox-catalysis to alkenes, giving rise to enantioenriched α-trialkyl-α-tertiary amines. This process exploits a commercially available phenylglycinol derivative as a source of both nitrogen and chiral information. DFT studies support a stereochemical model whereby an intramolecular H-bond rigidifies the transition state of the enantiodetermining step.

Description

Funder: AstraZeneca


Funder: Royal Society

Keywords
3402 Inorganic Chemistry, 3405 Organic Chemistry, 34 Chemical Sciences
Journal Title
Org Lett
Conference Name
Journal ISSN
1523-7060
1523-7052
Volume Title
25
Publisher
American Chemical Society (ACS)
Sponsorship
Engineering and Physical Sciences Research Council (EP/S020292/1)