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New Initiation Modes for Directed Carbonylative C-C Bond Activation: Rhodium-Catalyzed (3 + 1 + 2) Cycloadditions of Aminomethylcyclopropanes.

ABSTRACT: Under carbonylative conditions, neutral Rh(I)-systems modified with weak donor ligands (AsPh₃ or 1,4-oxathiane) undergo N-Cbz, N-benzoyl, or N-Ts directed insertion into the proximal C-C bond of aminomethylcyclopropanes to generate rhodacyclopentanone intermediates. These are trapped by N-tethered alkenes to provide complex perhydroisoindoles.

SUBMITTER: Wang GW

PROVIDER: S-EPMC5073370 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

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New Initiation Modes for Directed Carbonylative C-C Bond Activation: Rhodium-Catalyzed (3 + 1 + 2) Cycloadditions of Aminomethylcyclopropanes.

Wang Gang-Wei GW Wang Gang-Wei GW McCreanor Niall G NG Shaw Megan H MH Whittingham William G WG Bower John F JF

Journal of the American Chemical Society 20161006 41

Under carbonylative conditions, neutral Rh(I)-systems modified with weak donor ligands (AsPh<sub>3</sub> or 1,4-oxathiane) undergo N-Cbz, N-benzoyl, or N-Ts directed insertion into the proximal C-C bond of aminomethylcyclopropanes to generate rhodacyclopentanone intermediates. These are trapped by N-tethered alkenes to provide complex perhydroisoindoles. ...[more]

PMID: 27709913

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