CHIRALITY TRANSFER FROM NITROGEN TO CARBON IN THE [2,3]-MEISENHEIMER REARRANGEMENT

Authors
BUSTON JEH COLDHAM I MULHOLLAND KR
Citation
Jeh. Buston et al., CHIRALITY TRANSFER FROM NITROGEN TO CARBON IN THE [2,3]-MEISENHEIMER REARRANGEMENT, Synlett, (3), 1997, pp. 322
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
3
Year of publication
1997
Database
ISI
SICI code
0936-5214(1997):3<322:CTFNTC>2.0.ZU;2-6
Abstract
Oxidation of chiral, camphidin-based allylic tertiary amines gives ris e to chiral tertiary amine-N-oxides, which undergo the [2,3]Meisenheim er rearrangement with high levels of stereoselectivity. Reductive N,O- bond cleavage of the O-allyl-hydroxylamine gives access to the allylic alcohol unit.