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Carbonylative N-Heterocyclization via Nitrogen-Directed C-C Bond Activation of Nonactivated Cyclopropanes.

ABSTRACT: Under Rh-catalyzed conditions, secondary amines and anilines function as directing groups to facilitate regioselective C-C bond activation of nonactivated cyclopropanes. The resulting amino-stabilized rhodacycles undergo carbonylative C-N bond formation en route to challenging seven- and eight-membered lactams. The processes represent rare examples where C-C bond oxidative addition of nonactivated cyclopropanes is exploited in reaction design.

SUBMITTER: Calow ADJ

PROVIDER: S-EPMC9248011 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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Carbonylative N-Heterocyclization via Nitrogen-Directed C-C Bond Activation of Nonactivated Cyclopropanes.

Calow Adam D J ADJ Dailler David D Bower John F JF

Journal of the American Chemical Society 20220617 25

Under Rh-catalyzed conditions, secondary amines and anilines function as directing groups to facilitate regioselective C-C bond activation of nonactivated cyclopropanes. The resulting amino-stabilized rhodacycles undergo carbonylative C-N bond formation en route to challenging seven- and eight-membered lactams. The processes represent rare examples where C-C bond oxidative addition of nonactivated cyclopropanes is exploited in reaction design. ...[more]

PMID: 35715228

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