Pentadienyltitaniums as versatile intermediates: Regio- and stereoselectivities

Citation
A. Zellner et M. Schlosser, Pentadienyltitaniums as versatile intermediates: Regio- and stereoselectivities, SYNLETT, 2001, pp. 1016-1018
Citations number
20
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Year of publication
2001
Pages
1016 - 1018
Database
ISI
SICI code
0936-5214(2001):<1016:PAVIRA>2.0.ZU;2-#
Abstract
The adduct obtained upon consecutive treatment of 1,4-dienes with butyllith ium in the presence of potassium tert-butoxide, chlorotri(isopropyloxy)tita nium and a carbonyl compound contains the alpha -hydroxyalkyl group invaria bly and exclusively linked to the 3-position of the former diene. When chlo rotri(isopropyloxy)titanium is replaced by the Duthaler-Hafner reagent [(4R ,5R)-chloro(cyclopentadienyl)(2,2-dimethyl-alpha,alpha,alpha',alpha'-tetrap henyl-1,3-dioxolane-4,5-dimethanolato-O,O-alpha)titanium] the reaction does not only occur regioselectively but also with appreciably high enantiosele ctivity.