PI-FACIAL DIASTEREOSELECTIVITY IN ELECTROPHILIC ADDITIONS AND 1,3-DIPOLAR CYCLOADDITIONS TO BICYCLO[2.2.2]OCT-2-ENES 5,6-CIS,EXO-DISUBSTITUTED WITH ELECTRON-WITHDRAWING GROUPS

Authors
GANDOLFI R AMADE MS RASTELLI A BAGATTI M
Citation
R. Gandolfi et al., PI-FACIAL DIASTEREOSELECTIVITY IN ELECTROPHILIC ADDITIONS AND 1,3-DIPOLAR CYCLOADDITIONS TO BICYCLO[2.2.2]OCT-2-ENES 5,6-CIS,EXO-DISUBSTITUTED WITH ELECTRON-WITHDRAWING GROUPS, Tetrahedron letters, 37(8), 1996, pp. 1321-1324
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
8
Year of publication
1996
Pages
1321 - 1324
Database
ISI
SICI code
0040-4039(1996)37:8<1321:PDIEAA>2.0.ZU;2-6
Abstract
The high syn selectivity (e.g., synlanti greater than or equal to 83:1 7) observed in epoxidation of the torsionally and sterically unbiased 5,6-cis,exo-disubstitutedbicyclo[2.2.2]oct-2-enes (bearing electron wi thdrawing groups) progressively decreases on going to dihydroxylation and 1,3-dipolar cycloadditions, with practically no selectivity in the care of nitrones and dominance of anti attack in the reactions of dia zomethane (synlanti less than or equal to 32.68), in contrast with pre dictions bared on Cieplak's theory.