DIASTEREOSELECTIVE ENE REACTIONS OF TRIAZOLINEDIONES WITH CHIRAL ALLYLIC ALCOHOLS - EVIDENCE FOR A HYDROXYL-ENOPHILE STEERING EFFECT

Authors
STRATAKIS M VASSILIKOGIANNAKIS G ORFANOPOULOS M
Citation
M. Stratakis et al., DIASTEREOSELECTIVE ENE REACTIONS OF TRIAZOLINEDIONES WITH CHIRAL ALLYLIC ALCOHOLS - EVIDENCE FOR A HYDROXYL-ENOPHILE STEERING EFFECT, Tetrahedron letters, 39(16), 1998, pp. 2393-2396
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
16
Year of publication
1998
Pages
2393 - 2396
Database
ISI
SICI code
0040-4039(1998)39:16<2393:DEROTW>2.0.ZU;2-K
Abstract
The ene reaction of PTAD with the chiral allylic alcohol 4-methyl-3-pe nten-2-ol exhibits high three diastereoselectvity in non polar solvent s, whereas in polar solvents the diastereoselectivity decreases substa ntially. These results are discussed in terms of a steering effect bet ween the hydroxyl and the incoming enophile during: the formation elf the diastereomeric syn and anti aziridinium imide intermediates. (C) 1 998 Elsevier Science Ltd. All rights reserved.