A DRAMATIC REVERSAL OF FACIAL SELECTIVITY IN THE SHARPLESS ASYMMETRICDIHYDROXYLATION OF A STERICALLY HINDERED 3-METHYLIDENE-BENZOFURAN

Authors
KRYSAN DJ
Citation
Dj. Krysan, A DRAMATIC REVERSAL OF FACIAL SELECTIVITY IN THE SHARPLESS ASYMMETRICDIHYDROXYLATION OF A STERICALLY HINDERED 3-METHYLIDENE-BENZOFURAN, Tetrahedron letters, 37(9), 1996, pp. 1375-1376
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
9
Year of publication
1996
Pages
1375 - 1376
Database
ISI
SICI code
0040-4039(1996)37:9<1375:ADROFS>2.0.ZU;2-C
Abstract
A dramatic reversal of pi-facial selectivity in the osmium-catalyzed a symmetric dihydroxylation (AD) of an exocyclic olefin is reported; whe rein, switching from a phthalazine-linked ligand to a pyrimidine-linke d ligand led to the opposite enantiomer using the same psuedoenantiome r of the cinchona alkaloid.