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Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters.

ABSTRACT: Herein, we report a Zn-ProPhenol catalyzed direct asymmetric amination reaction of unactivated aryl and vinyl ketones using di-tert-butyl azodicarboxylate as a cheap and practical electrophilic nitrogen source. Importantly, this methodology works with both ?-branched and unbranched ketones for the construction of tri- and tetrasubstituted N-containing stereocenters. The reaction can be run at gram-scale with low catalyst loadings and features a recoverable and reusable ligand. Finally, the enantioenriched hydrazine products can be readily converted into versatile building blocks such as ?-amino carbonyl compounds and ?-amino alcohols.

SUBMITTER: Trost BM

PROVIDER: S-EPMC5897889 | biostudies-other | 2018 Mar

REPOSITORIES: biostudies-other

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Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters.

Trost B M BM Tracy J S JS Saget T T

Chemical science 20180214 11

Herein, we report a Zn-ProPhenol catalyzed direct asymmetric amination reaction of unactivated aryl and vinyl ketones using di-<i>tert</i>-butyl azodicarboxylate as a cheap and practical electrophilic nitrogen source. Importantly, this methodology works with both α-branched and unbranched ketones for the construction of tri- and tetrasubstituted N-containing stereocenters. The reaction can be run at gram-scale with low catalyst loadings and features a recoverable and reusable ligand. Finally, th ...[more]

PMID: 29719678

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