A MECHANISTICALLY DESIGNED MONO-CINCHONA ALKALOID IS AN EXCELLENT CATALYST FOR THE ENANTIOSELECTIVE DIHYDROXYLATION OF OLEFINS

Authors
COREY EJ NOE MC GROGAN MJ
Citation
Ej. Corey et al., A MECHANISTICALLY DESIGNED MONO-CINCHONA ALKALOID IS AN EXCELLENT CATALYST FOR THE ENANTIOSELECTIVE DIHYDROXYLATION OF OLEFINS, Tetrahedron letters, 35(35), 1994, pp. 6427-6430
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
35
Year of publication
1994
Pages
6427 - 6430
Database
ISI
SICI code
0040-4039(1994)35:35<6427:AMDMAI>2.0.ZU;2-R
Abstract
On the basis of ideas recently advanced regarding the origin of enanti oselectivity in the OsO4-promoted dihydroxylation of olefins catalyzed by bis-cinchona alkaloid derivatives such as 1, specifically strong e vidence for reaction via transition stale assembly 2, the mono-quinidi ne derivative 3 was selected as a promising catalytic ligand. The expe rimental observation of high enantioselectivity promoted by 3 provides additional evidence in favor of transition-state 2.