Improved conditions for the addition of alkoxides to di(ethylene glycol) di-p-tosylate: application to the stereospecific synthesis of the trans-isomers of dicyclohexano-18-crown-6

Authors
Huber, VJ Dietz, ML
Citation
Vj. Huber et Ml. Dietz, Improved conditions for the addition of alkoxides to di(ethylene glycol) di-p-tosylate: application to the stereospecific synthesis of the trans-isomers of dicyclohexano-18-crown-6, TETRAHEDR L, 42(16), 2001, pp. 2945-2948
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
16
Year of publication
2001
Pages
2945 - 2948
Database
ISI
SICI code
0040-4039(20010416)42:16<2945:ICFTAO>2.0.ZU;2-N
Abstract
Conditions are defined for the efficient preparation of polyethers by direc t condensation of ditosylates and alkoxides, and this approach is shown to provide a facile method for the synthesis of the trans-syn-trans (C) and tr ans-anti-trans (D) isomers of dicyclohexano-18-crown-6 (DCH18C6), one which both provides significantly improved yields and avoids the difficult separ ations required by certain previously described synthetic methods. (C) 2001 Elsevier Science Ltd. All rights reserved.