PHOSPHORAMIDITES DERIVED FROM TERTIARY ALCOHOLS - WHY DO THEY SOMETIMES COUPLE WITH LOW EFFICIENCY

Authors
SCHEUERLARSEN C DAHL BM WENGEL J DAHL O
Citation
C. Scheuerlarsen et al., PHOSPHORAMIDITES DERIVED FROM TERTIARY ALCOHOLS - WHY DO THEY SOMETIMES COUPLE WITH LOW EFFICIENCY, Tetrahedron letters, 39(45), 1998, pp. 8361-8364
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
45
Year of publication
1998
Pages
8361 - 8364
Database
ISI
SICI code
0040-4039(1998)39:45<8361:PDFTA->2.0.ZU;2-8
Abstract
tert-Alkyl phosphoramidites are somewhat sterically hindered, but give phosphites in good yields with tetrazole catalysis when the coupling time with alcohols is prolonged. Low yields of phosphotriesters are ca used by elimination of the tertiary alkyl group during the subsequent oxidation of the phosphite with iodine/water/pyridine, and can be avoi ded by the use of tert-butyl hydroperoxide as the oxidant. (C) 1998 El sevier Science Ltd. All rights reserved.