ISSN:
0009-2940
Schlagwort(e):
Dimethyldioxirane
;
3-Phenyl-2-phenylsulfonyloxaziridine
;
Titanium enolates
;
Enantioselective hydroxylation
;
α-Hydroxy carbonyl compounds
;
Chemistry
;
Inorganic Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
The stereoselective oxidation of the optically active titanium enolate complexes 2 of propiophenone by dimethyldioxirane (3) (as acetone solution) and 3-Phenyl-2-phenylsulfonyloxaziridine (4) has been investigated. The chiral titanium enolates 2 were synthesized by the reaction of the lithium enolate of propiophenone and the respective optically active chlorotitanate complexes 1. For 3 as oxidant, the stereoselectivity of the α hydroxylation strongly depends on the substitution pattern at the central titanium atom and reached for the best case, namely 2e, an enantiomeric excess (ee) of 63%. Solvent and temperature exhibited only small effects on the stereoselectivity. Compound 4 as oxidant gave lower enantiomeric excesses than 3.
Zusätzliches Material:
1 Tab.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/cber.19941270415
