ePrints

Highly Efficient Asymmetric Lewis Acid Catalysis with Platinum Group Complexes of Conformationally Flexible 1,3-Butadiene-Bridged Diphosphines, NUPHOS

Lookup NU author(s): Dr Simon DohertyORCiD, Dr Rakesh Rath, Dr Julian Knight

Downloads

Full text for this publication is not currently held within this repository. Alternative links are provided below where available.

Abstract

(Matrix presented). Palladium and platinum complexes of conformationally flexible 1,3-butadiene-bridged diphosphines NUPHOS can be resolved with (S)-BINOL at elevated temperatures to afford diastereopure δ-[(NUPHOS) M{(S)-BINOL}] (M = Pd, Pt). The homochiral Lewis acid complexes δ-[(NUPHOS)M]-[OTf]2, generated by protonation of δ-[(NUPHOS)M{(S)-BINOL}] with trifluoromethanesulfonic acid, catalyze the Diels-Alder reaction between acryloyl-N-oxazolidinones and cyclopentadiene to give ee values up to 96%. The corresponding enantiopure dichlorides δ-[(NUPHOS)PtCl2] react with AgClO4 to form highly efficient catalysts that give good endo/exo selectivities and high endo enantioselectivity.

Publication metadata

Author(s): Doherty S, Newman CR, Rath RK, Luo H-K, Nieuwenhuyzen M, Knight JG

Publication type: Article

Publication status: Published

Journal: Organic Letters

Year: 2003

Volume: 5

Issue: 21

Pages: 3863-3866

ISSN (print): 1523-7060

ISSN (electronic): 1523-7052

Publisher: American Chemical Society

URL: http://dx.doi.org/10.1021/ol035409i

DOI: 10.1021/ol035409i

Altmetrics

Share