Phosphites and diamidophosphites based on mono-ethers of BINOL: a comparison of enantioselectivity in asymmetric catalytic reactions

Novel P-monodentate phosphite-type ligands have been synthesized in one step from BINOL mono-tosylate and BINOL mono-(−)-menthylcarbonate. The use of these ligands provides up to 96% ee in Pd-catalyzed asymmetric allylic substitution of ( E)-1,3-diphenylallyl acetate and up to 99% ee in Rh-catalyzed...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2012-02, Vol.68 (5), p.1581-1589
Main Authors: Gavrilov, Konstantin N., Zheglov, Sergey V., Gavrilova, Mariya N., Novikov, Ivan M., Maksimova, Marina G., Groshkin, Nikolay N., Rastorguev, Eugenie A., Davankov, Vadim A.
Format: Article
Language:English
Subjects:
Asymmetric addition
Asymmetric allylic substitution
Diamidophosphites
Palladium
Phosphites
Rhodium
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Novel P-monodentate phosphite-type ligands have been synthesized in one step from BINOL mono-tosylate and BINOL mono-(−)-menthylcarbonate. The use of these ligands provides up to 96% ee in Pd-catalyzed asymmetric allylic substitution of ( E)-1,3-diphenylallyl acetate and up to 99% ee in Rh-catalyzed asymmetric addition of phenylboronic acid to cyclohex-2-enone. The influence of the structural modules such as the nature of phosphorus-containing ring or exocyclic substituent on the enantioselectivity is discussed. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.11.092