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

Author(s): Annette Wolfgardt , Franz Bracher .

Journal Name: Letters in Organic Chemistry

Volume 10 , Issue 1 , 2013

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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.

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

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Article Details

Year: 2013
Page: [2 - 7]
Pages: 6
DOI: 10.2174/1570178611310010003

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