A CAVEAT ON THE SHARPLESS ASYMMETRIC DIHYDROXYLATION

Authors
IWASHIMA M KINSHO T SMITH AB
Citation
M. Iwashima et al., A CAVEAT ON THE SHARPLESS ASYMMETRIC DIHYDROXYLATION, Tetrahedron letters, 36(13), 1995, pp. 2199-2202
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
13
Year of publication
1995
Pages
2199 - 2202
Database
ISI
SICI code
0040-4039(1995)36:13<2199:ACOTSA>2.0.ZU;2-R
Abstract
Sharpless asymmetric dihydroxylation (AD) of the homochiral synthetic intermediates 2a-c gave anomalous results: pairs of pseudoenantiomeric reagents, expected to generate complementary diastereomer ratios char acteristic of double diastereoselection, instead generally furnished i ndistinguishable product mixtures. AD reactions of related monosubstit uted olefins failed to pinpoint the structural features responsible fo r the unexpected behavior.