Conversion of Phenols into Aryl Tert-Butyl Ethers Under Mitsunobu Conditions Utilizing Neighboring Group Contribution

Title:Conversion of Phenols into Aryl Tert-Butyl Ethers Under Mitsunobu Conditions Utilizing Neighboring Group Contribution

Volume: 10 Issue: 1

Author(s): Annette Wolfgardt and Franz Bracher

Affiliation:

Keywords: N-Boc-aminoalcohols, tert-butyl ether, Mitsunobu reaction, neighboring group contribution, protecting group, stereoselective reaction, contaminant, neutral, triphosgene

Abstract: Under Mitsunobu conditions N-Boc-2-(hydroxymethyl)piperidine acts as a source of tert-butyl residue for the conversion of phenols into aryl tert-butyl ethers under neutral conditions. This reactivity can be attributed to a neighboring group contribution which strongly depends on the structure of the employed N-Boc-aminoalcohol. Five other, closely related N-Boc-aminoalcohols investigated here did not show this special reactivity, and gave the regular Mitsunobu coupling products.

Cite this article as:

Wolfgardt Annette and Bracher Franz, Conversion of Phenols into Aryl Tert-Butyl Ethers Under Mitsunobu Conditions Utilizing Neighboring Group Contribution, Letters in Organic Chemistry 2013; 10 (1) . https://dx.doi.org/10.2174/1570178611310010003