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Three-Component 1,2-Carboamidation of Bridged Bicyclic Alkenes via Rh^III-Catalyzed Addition of C-H Bonds and Amidating Reagents.

ABSTRACT: A three-component method is described for the preparation of syn-1,2-disubstituted bridged bicyclic compounds. The reaction was demonstrated for readily available aromatic and heteroaromatic C-H bond substrates with tertiary and secondary amide, lactam, pyrazole, and triazole directing groups and a variety of bridged bicyclic alkenes, including norbornene, benzonorbornadiene, oxygen- and nitrogen-bridged analogs, and an unsaturated tropinone. A broad dioxazolone scope was also observed. The use of a chiral Cp-derived Rh^III catalyst enables asymmetric synthesis of products.

SUBMITTER: Brandes DS

PROVIDER: S-EPMC8026749 | biostudies-literature | 2021 Apr

REPOSITORIES: biostudies-literature

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Three-Component 1,2-Carboamidation of Bridged Bicyclic Alkenes via RhIII-Catalyzed Addition of C-H Bonds and Amidating Reagents.

Brandes Daniel S DS Sirvent Ana A Mercado Brandon Q BQ Ellman Jonathan A JA

Organic letters 20210319 7

A three-component method is described for the preparation of syn-1,2-disubstituted bridged bicyclic compounds. The reaction was demonstrated for readily available aromatic and heteroaromatic C-H bond substrates with tertiary and secondary amide, lactam, pyrazole, and triazole directing groups and a variety of bridged bicyclic alkenes, including norbornene, benzonorbornadiene, oxygen- and nitrogen-bridged analogs, and an unsaturated tropinone. A broad dioxazolone scope was also observed. T ...[more]

PMID: 33739839

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