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Enantioselective palladaelectro-catalyzed C-H olefinations and allylations for N-C axial chirality.

ABSTRACT: Enantioselective palladaelectro-catalyzed C-H alkenylations and allylations were achieved with easily-accessible amino acids as transient directing groups. This strategy provided access to highly enantiomerically-enriched N-C axially chiral scaffolds under exceedingly mild conditions. The synthetic utility of our strategy was demonstrated by a variety of alkenes, while the versatility of our approach was reflected by atroposelective C-H allylations. Computational studies provided insights into a facile C-H activation by a seven-membered palladacycle.

SUBMITTER: Dhawa U

PROVIDER: S-EPMC8565398 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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Enantioselective palladaelectro-catalyzed C-H olefinations and allylations for N-C axial chirality.

Dhawa Uttam U Wdowik Tomasz T Hou Xiaoyan X Yuan Binbin B Oliveira João C A JCA Ackermann Lutz L

Chemical science 20211013 42

Enantioselective palladaelectro-catalyzed C-H alkenylations and allylations were achieved with easily-accessible amino acids as transient directing groups. This strategy provided access to highly enantiomerically-enriched N-C axially chiral scaffolds under exceedingly mild conditions. The synthetic utility of our strategy was demonstrated by a variety of alkenes, while the versatility of our approach was reflected by atroposelective C-H allylations. Computational studies provided insights into a ...[more]

PMID: 34760203

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