Stereoselective synthesis of optically active phenyl ethers

Authors
Said, SA Fiksdahl, A Carlsen, PHJ
Citation
Sa. Said et al., Stereoselective synthesis of optically active phenyl ethers, TETRAHEDR L, 41(29), 2000, pp. 5593-5596
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
29
Year of publication
2000
Pages
5593 - 5596
Database
ISI
SICI code
0040-4039(20000715)41:29<5593:SSOOAP>2.0.ZU;2-C
Abstract
Reacting the 1,2-naphthalenedisulfonimide of (S)-alpha-methylbenzylamine wi th phenol gave the corresponding alpha-methylbenzyl phenyl ether with 46% e .e. Synthesis of the authentic optically active phenyl ethers was accomplis hed under mild, neutral conditions by generating benzyne in the presence of optically active (R)-alpha-methylbenzyl alcohol. Benzyne was generated by reacting anthranilic acid with tert-butyl nitrite in refluxing monoglyme. ( C) 2000 Elsevier Science Ltd. All rights reserved.