ENANTIOSELECTIVE SYNTHESIS OF ALPHA-PHOSP HINOLIETONES

Authors
ENDERS D BERG T RAABE G RUNSINK J
Citation
D. Enders et al., ENANTIOSELECTIVE SYNTHESIS OF ALPHA-PHOSP HINOLIETONES, Helvetica Chimica Acta, 79(1), 1996, pp. 118-122
Citations number
52
Categorie Soggetti
Chemistry
Journal title
Helvetica Chimica Acta → ACNP
ISSN journal
0018019X
Volume
79
Issue
1
Year of publication
1996
Pages
118 - 122
Database
ISI
SICI code
0018-019X(1996)79:1<118:ESOAH>2.0.ZU;2-X
Abstract
The first asymmetric (C-P)-connective synthesis of alpha-phosphinoketo nes in high enantiomeric purity (e.e. 91-97 %) is described. Key step is the highly diastereoselective phosphinylation of SAMP-hydrazones (S )-2 to produce alpha-phosphinohydrazones (S,R)-3, isolated as the more stable borane adducts. Subsequent ozonolysis afforded the title compo unds (R)-4, potential ligands for enantioselective homogeneous catalys is.