1104739-90-3Relevant academic research and scientific papers
Phosphinooxazolines derived from 3-amino-1,2-diols: Highly efficient modular P-N ligands
Popa, Dana,Puigjaner, Cristina,Gomez, Montserrat,Benet-Buchholz, Jordi,Vidal-Ferran, Anton,Pericas, Miquel A.
, p. 2265 - 2278 (2008/09/19)
A family of chiral phosphinooxazolines (12a-e) derived from modular, enantiopure β-amino alcohols has been prepared, and their palladium complexes have been used as chiral mediators in the asymmetric allylic alkylation reaction. The oxazoline moiety in 12 contains a C-4 aryl and a C-5 alkoxymethyl substituent that can be independently optimized for high catalytic activity and enantioselectivity. A methoxymethyl substituent at C-5 has beenfound to provide the best results in terms of enantioselectivity and activity in the alkylation of a diverse family of allylic substrates under both thermal and microwave-assisted activation. The palladium-phos- phinooxazoline complexes described in this work are remarkably robust, as the enantioselectivity recorded in the asymmetric allylic alkylation remains essentially unchanged in the temperature range between 20 and 130°C. An unprecedented reversal in enantioselectivity has been observed between 1, 3-diphe-nylallyl and 1,3-dimethylallyl alkylation substrates, and the origin of this behavior has beeh explained by means of ONIOM QM/MM calculations.
