REVERSAL OF REGIOSELECTION IN THE ASYMMETRIC AMINOHYDROXYLATION OF CINNAMATES

Authors
TAO B SCHLINGLOFF G SHARPLESS KB
Citation
B. Tao et al., REVERSAL OF REGIOSELECTION IN THE ASYMMETRIC AMINOHYDROXYLATION OF CINNAMATES, Tetrahedron letters, 39(17), 1998, pp. 2507-2510
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
17
Year of publication
1998
Pages
2507 - 2510
Database
ISI
SICI code
0040-4039(1998)39:17<2507:RORITA>2.0.ZU;2-4
Abstract
Use of cinchona ligands with an anthraquinone (AQN) core, in place of the usual phthalazine (PHAL) core, in the asymmetric aminohydroxylatio n of cinnamates causes dramatic reversal of the regioselection, so tha t phenyl serines are obtained in high enantiomeric excess. Hence, the regioselectivity outcome (i.e. isoserine vs. serine) is controlled by the ligand and not the substrate. (C) 1998 Elsevier Science Ltd. All r ights reserved.