DIASTEREOSELECTIVE ADDITION OF ORGANOMETALLIC REAGENTS TO NOR-EPHEDRINE-DERIVED 2-ACYL-N-TOSY-OXAZOLDINES

Authors
POLI G MACCAGNI E MANZONI L PILATI T SCOLASTICO C
Citation
G. Poli et al., DIASTEREOSELECTIVE ADDITION OF ORGANOMETALLIC REAGENTS TO NOR-EPHEDRINE-DERIVED 2-ACYL-N-TOSY-OXAZOLDINES, Synlett, (1), 1995, pp. 71-73
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
1
Year of publication
1995
Pages
71 - 73
Database
ISI
SICI code
0936-5214(1995):1<71:DAOORT>2.0.ZU;2-Q
Abstract
Addition of carbanionic reagents to the 2-acyl-N-tosyl-oxazolidines 1 and 11 has been studied. Organolithium and organomagnesium reagents ad d to the methyl ketone I with remarkable Re and Si pi-face selectivity respectively. With phenyl ketone 11 only organomagnesium reagents fol low the above trend. Models accounting for the observed stereochemical behavior are proposed.