e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Organic letters

Converting gem-Dimethyl Groups into Cyclopropanes via Pd-Catalyzed Sequential CH Activation and Radical Cyclization

R Giri, M Wasa, SP Breazzano, JQ Yu

Index: Giri, Ramesh; Wasa, Masayuki; Breazzano, Steven P.; Yu, Jin-Quan Organic Letters, 2006 , vol. 8, # 25 p. 5685 - 5688

Full Text: HTML

Citation Number: 52

Abstract

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 CH 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.

Butanoic acid,2,2,3,3-tetramethyl- Structure

Butanoic acid,2...

~%

4,4-dimethyl-2-(2,3,3-trimethylbutan-2-yl)-5H-1,3-oxazole Structure

4,4-dimethyl-2-...

2,2,3,3-tetramethylbutyric acid chloride Structure

2,2,3,3-tetrame...

~%

4,4-dimethyl-2-(2,3,3-trimethylbutan-2-yl)-5H-1,3-oxazole Structure

4,4-dimethyl-2-...

Propanoic acid,3-bromo-2,2-dimethyl- Structure

Propanoic acid,...

~%

2-(1-bromo-2-methylpropan-2-yl)-4,4-dimethyl-5H-1,3-oxazole Structure

2-(1-bromo-2-me...

2-tert-pentyl-4,4-dimethyl-4,5-dihydrooxazole Structure

2-tert-pentyl-4...

~82%

2-[1-iodo-2-(iodomethyl)butan-2-yl]-4,4-dimethyl-5H-1,3-oxazole Structure

2-[1-iodo-2-(io...

2,2-Dimethylbutanoic acid Structure

2,2-Dimethylbut...

~%

2-[1-iodo-2-(iodomethyl)butan-2-yl]-4,4-dimethyl-5H-1,3-oxazole Structure

2-[1-iodo-2-(io...

2,2-Dimethylbutanoyl chloride Structure

2,2-Dimethylbut...

~%

2-[1-iodo-2-(iodomethyl)butan-2-yl]-4,4-dimethyl-5H-1,3-oxazole Structure

2-[1-iodo-2-(io...

(2-methylhexan-2-yl)-4,4-dimethyl-4,5-dihydrooxazole Structure

(2-methylhexan-...

~85%

2-[1-iodo-2-(iodomethyl)hexan-2-yl]-4,4-dimethyl-5H-1,3-oxazole Structure

2-[1-iodo-2-(io...

Hexanoic acid,2,2-dimethyl- Structure

Hexanoic acid,2...

~%

2-[1-iodo-2-(iodomethyl)hexan-2-yl]-4,4-dimethyl-5H-1,3-oxazole Structure

2-[1-iodo-2-(io...

2-(1-chloro-2-methylpropan-2-yl)-4,4-dimethyl-5H-1,3-oxazole Structure

2-(1-chloro-2-m...

~67%

2-[1-chloro-3-iodo-2-(iodomethyl)propan-2-yl]-4,4-dimethyl-5H-1,3-oxazole Structure

2-[1-chloro-3-i...

Chloropivaloyl chloride Structure

Chloropivaloyl ...

~%

2-[1-chloro-3-iodo-2-(iodomethyl)propan-2-yl]-4,4-dimethyl-5H-1,3-oxazole Structure

2-[1-chloro-3-i...

Propanoic acid,3-chloro-2,2-dimethyl- Structure

Propanoic acid,...

~%

2-[1-chloro-3-iodo-2-(iodomethyl)propan-2-yl]-4,4-dimethyl-5H-1,3-oxazole Structure

2-[1-chloro-3-i...

2-[1-iodo-2-(iodomethyl)butan-2-yl]-4,4-dimethyl-5H-1,3-oxazole Structure

2-[1-iodo-2-(io...

~83%

2-(1-ethylcyclopropyl)-4,4-dimethyl-5H-1,3-oxazole Structure

2-(1-ethylcyclo...

2,2-Dimethylbutanoic acid Structure

2,2-Dimethylbut...

~%

2-(1-ethylcyclopropyl)-4,4-dimethyl-5H-1,3-oxazole Structure

2-(1-ethylcyclo...

2,2-Dimethylbutanoyl chloride Structure

2,2-Dimethylbut...

~%

2-(1-ethylcyclopropyl)-4,4-dimethyl-5H-1,3-oxazole Structure

2-(1-ethylcyclo...

2-tert-pentyl-4,4-dimethyl-4,5-dihydrooxazole Structure

2-tert-pentyl-4...

~%

2-(1-ethylcyclopropyl)-4,4-dimethyl-5H-1,3-oxazole Structure

2-(1-ethylcyclo...

Chloropivaloyl chloride Structure

Chloropivaloyl ...

~%

2-(1-chloro-2-methylpropan-2-yl)-4,4-dimethyl-5H-1,3-oxazole Structure

2-(1-chloro-2-m...

Propanoic acid,3-chloro-2,2-dimethyl- Structure

Propanoic acid,...

~%

2-(1-chloro-2-methylpropan-2-yl)-4,4-dimethyl-5H-1,3-oxazole Structure

2-(1-chloro-2-m...