Work

An Improved Method for the Protection of Carboxylic Acids as 1,1-Dimethylallyl Esters

Year: 2006

Type: article

Abstract: 1,1-Dimethylallyl (DMA) esters of various N-protected amino acids have been synthesized using prenyldimethylsulfonium tetrafluroborate, a reagent that can be readily made and stored, in conjunction with catalytic CuBr. These reactions were complete within several hours and afforded DMA esters in high yields. As has been previously shown in our group, DMA esters represent a palladium-labile proctecting group for carboxylic acids that resists nucleophilic attack as a tert-butyl ester would.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo061207z

Authors: Minoo Sedighi, Selçuk Çalimsiz, Mark A. Lipton

Institution: Purdue University West Lafayette

Language: English

Topic: Chemical Synthesis and Analysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of Allergy and Infectious Diseases

Award: Studies of Antitumor,Anti HIV Cyclic Depsipeptides