Stereoselective synthesis of optically active phenyl ethers

Reacting the 1,2-naphthalenedisulfonimide of ( S)-α-methylbenzylamine with phenol gave the corresponding α-methylbenzyl phenyl ether with 46% e.e. Synthesis of the authentic optically active phenyl ethers was accomplished under mild, neutral conditions by generating benzyne in the presence of optica...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 41; no. 29; pp. 5593 - 5596
Main Authors Said, Sadri A, Fiksdahl, Anne, Carlsen, Per H.J
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.07.2000
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PHENOLS
Online AccessGet full text

Cover

More Information
Summary:Reacting the 1,2-naphthalenedisulfonimide of ( S)-α-methylbenzylamine with phenol gave the corresponding α-methylbenzyl phenyl ether with 46% e.e. Synthesis of the authentic optically active phenyl ethers was accomplished under mild, neutral conditions by generating benzyne in the presence of optically active ( R)-α-methylbenzyl alcohol. Benzyne was generated by reacting anthranilic acid with tert-butyl nitrite in refluxing monoglyme.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)00872-8