Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 20, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202200105
Keywords
Amino Acids; Dienol Ethers; Palladium; Photoredox; Stereoselectivity
Categories
Funding
- Chinese Scholarship Council
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The study presents a highly regio-, diastereo-, and enantioselective intermolecular hydroaminoalkylation (HAA) of alkenes using a unified photoredox and palladium catalytic system, allowing for the construction of vicinal amino tertiary ethers with exceptional levels of selectivity. The key step in the mechanism is shown to be a reversible hydropalladation.
Intermolecular photocatalytic hydroaminoalkylation (HAA) of alkenes have emerged as a powerful method for the construction of alkyl amines. Although there are some studies aiming at stereoselective photocatalytic HAA reactions, the alkenes are limited to electrophilic alkenes. Herein, we report a highly regio-, diastereo-, and enantioselective HAA of electron-rich dienol ethers and alpha-amino radicals derived from alpha-amino acids using a unified photoredox and palladium catalytic system. This decarboxylative 1,2-Markovnikov addition enables the construction of vicinal amino tertiary ethers with high levels of regio- (up to >19 : 1 rr), diastereo- (up to >19 : 1 dr), and enantioselectivity control (up to >99 % ee). Mechanistic studies support a reversible hydropalladation as a key step.
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