Converting gem-dimethyl groups into cyclopropanes via Pd-catalyzed sequential C-H activation and radical cyclization

Ramesh Giri; Masayuki Wasa; Steven P. Breazzano; Jin Quan Yu

doi:10.1021/ol0618858

Converting gem-dimethyl groups into cyclopropanes via Pd-catalyzed sequential C-H activation and radical cyclization

Ramesh Giri, Masayuki Wasa, Steven P. Breazzano, Jin Quan Yu

Chemistry

Research output: Contribution to journal › Article › peer-review

66 Scopus citations

Abstract

(Diagram presented) A novel route to the synthesis of cyclopropane derivatives is described. 1,1-Dimethyls in 2-(1,1-dimethylalkyl) dimethyloxazolines are first converted into 1,3-diiodide derivatives via Pd-catalyzed sequential C-H activation and then radically cyclized to provide 2-(1-alkylcylclopropyl)-dimethyloxazolines. The use of EtOAc as a solvent is crucial for the diiodination of the functionalized substrates.

Original language	English (US)
Pages (from-to)	5685-5688
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	25
DOIs	https://doi.org/10.1021/ol0618858
State	Published - Dec 7 2006

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0618858

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abstract = "(Diagram presented) A novel route to the synthesis of cyclopropane derivatives is described. 1,1-Dimethyls in 2-(1,1-dimethylalkyl) dimethyloxazolines are first converted into 1,3-diiodide derivatives via Pd-catalyzed sequential C-H activation and then radically cyclized to provide 2-(1-alkylcylclopropyl)-dimethyloxazolines. The use of EtOAc as a solvent is crucial for the diiodination of the functionalized substrates.",

author = "Ramesh Giri and Masayuki Wasa and Breazzano, \{Steven P.\} and Yu, \{Jin Quan\}",

year = "2006",

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language = "English (US)",

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journal = "Organic Letters",

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publisher = "American Chemical Society",

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T1 - Converting gem-dimethyl groups into cyclopropanes via Pd-catalyzed sequential C-H activation and radical cyclization

AU - Giri, Ramesh

AU - Wasa, Masayuki

AU - Breazzano, Steven P.

AU - Yu, Jin Quan

PY - 2006/12/7

Y1 - 2006/12/7

N2 - (Diagram presented) A novel route to the synthesis of cyclopropane derivatives is described. 1,1-Dimethyls in 2-(1,1-dimethylalkyl) dimethyloxazolines are first converted into 1,3-diiodide derivatives via Pd-catalyzed sequential C-H activation and then radically cyclized to provide 2-(1-alkylcylclopropyl)-dimethyloxazolines. The use of EtOAc as a solvent is crucial for the diiodination of the functionalized substrates.

AB - (Diagram presented) A novel route to the synthesis of cyclopropane derivatives is described. 1,1-Dimethyls in 2-(1,1-dimethylalkyl) dimethyloxazolines are first converted into 1,3-diiodide derivatives via Pd-catalyzed sequential C-H activation and then radically cyclized to provide 2-(1-alkylcylclopropyl)-dimethyloxazolines. The use of EtOAc as a solvent is crucial for the diiodination of the functionalized substrates.

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U2 - 10.1021/ol0618858

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JO - Organic Letters

JF - Organic Letters

IS - 25

ER -

Converting gem-dimethyl groups into cyclopropanes via Pd-catalyzed sequential C-H activation and radical cyclization

Abstract

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