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. 2016 Sep 14;138(36):11465-8.
doi: 10.1021/jacs.6b07046. Epub 2016 Sep 2.

Capture-Collapse Heterocyclization: 1,3-Diazepanes by C-N Reductive Elimination from Rhodacyclopentanones

Niall G McCreanor  1 , Steven Stanton  1 , John F Bower  1
Affiliations

Capture-Collapse Heterocyclization: 1,3-Diazepanes by C-N Reductive Elimination from Rhodacyclopentanones

Niall G McCreanor et al. J Am Chem Soc. .

Abstract

Rhodacyclopentanones derived from carbonylative C-C activation of cyclopropyl ureas can be "captured" by pendant nucleophiles prior to "collapse" to 1,3-diazepanes. The choice of N-substituent on the cyclopropane unit controls the oxidation level of the product, such that C4-C5 unsaturated or saturated systems can be accessed selectively.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1
Scheme 2
Scheme 2. Serial Rh-Catalyzed and Brønsted Acid Promoted Cyclizations
Scheme 3
Scheme 3
Scheme 4
Scheme 4
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