Issue 11, 2011
From the journal:

Chemical Communications

Guiding the nitrogen nucleophile to the middle: palladium-catalyzed decarboxylative cyclopropanation of 2-alkylidenetrimethylene carbonates with isocyanates†

Ryo Shintani,*a   Kohei Moriyaa  and  Tamio Hayashi*a  

* Corresponding authors

a Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan
E-mail: shintani@kuchem.kyoto-u.ac.jp, thayashi@kuchem.kyoto-u.ac.jp
Fax: +81 75-753-3988
Tel: +81 75-753-3983

Abstract

A palladium-catalyzed decarboxylative cyclopropanation of 2-alkylidenetrimethylene carbonates with isocyanates is described to form oxazolidinones of (1-aminocyclopropyl)methanols with high selectivity. The site of nucleophilic attack is directed by connecting the two reaction components and by employing an electron-deficient triarylphosphine ligand.

Graphical abstract: Guiding the nitrogen nucleophile to the middle: palladium-catalyzed decarboxylative cyclopropanation of 2-alkylidenetrimethylene carbonates with isocyanates

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Article information

DOI
https://doi.org/10.1039/C0CC05308B
Article type
Communication
Submitted
01 Dec 2010
Accepted
19 Jan 2011
First published
08 Feb 2011

Chem. Commun., 2011,47, 3057-3059

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Guiding the nitrogen nucleophile to the middle: palladium-catalyzed decarboxylative cyclopropanation of 2-alkylidenetrimethylene carbonates with isocyanates

R. Shintani, K. Moriya and T. Hayashi, Chem. Commun., 2011, 47, 3057 DOI: 10.1039/C0CC05308B

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