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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

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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

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