New ferrocenyloxazoline for the preparation of ferrocenes with planar chirality

Citation
E. Manoury et al., New ferrocenyloxazoline for the preparation of ferrocenes with planar chirality, ORGANOMETAL, 19(18), 2000, pp. 3736-3739
Citations number
31
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANOMETALLICS
ISSN journal
0276-7333 → ACNP
Volume
19
Issue
18
Year of publication
2000
Pages
3736 - 3739
Database
ISI
SICI code
0276-7333(20000904)19:18<3736:NFFTPO>2.0.ZU;2-R
Abstract
New ferrocenyloxazolines with two stereogenic centers were prepared with ex cellent yields starting from the (1S, 2S)-(+)-2-amino-3-phenyl-1, 3-propane diol. They can then be used for the preparation of ferrocenes with planar c hirality with very high diastereoselectivities (>99:1%) by a lithiation /el ectrophile-trapping sequence. The syntheses of chiral (phosphinoferrocenyl) oxazoline and (phenylthioferrocenyl)oxazoline and their use as ligands in c onjunction with bis[(pi-allyl)palladium chloride] in the enantioselective a llylic alkylation of rac-1,3-diphenylprop-2-enyl acetate was investigated.