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

Autor:	Harris, Georgia R, Trowbridge, Aaron D, Gaunt, Matthew J
Přispěvatelé:	Harris, Georgia R [0000-0001-9076-1505], Gaunt, Matthew J [0000-0002-7214-608X], Apollo - University of Cambridge Repository
Rok vydání:	2023
Předmět:	3402 Inorganic Chemistry 34 Chemical Sciences Organic Chemistry 3405 Organic Chemistry Physical and Theoretical Chemistry Biochemistry
Zdroj:	Organic Letters. 25:861-866
ISSN:	1523-7052 1523-7060
Popis:	Funder: AstraZeneca Funder: Royal Society 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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::4d9c230810d1f11334c67ffea0158712 https://doi.org/10.1021/acs.orglett.2c04308 Zobrazit plný text záznamu