Development of Diamidophosphite Ligands and Their Application to the Palladium-Catalyzed Vinyl-Substituted Trimethylenemethane Asymmetric [3 + 2] Cycloaddition

Development of Diamidophosphite Ligands and Their Application to the Palladium-Catalyzed Vinyl-Substituted Trimethylenemethane Asymmetric [3 + 2] Cycloaddition

A palladium-catalyzed asymmetric [3 + 2] cycloaddition of a vinyl-substituted trimethylenemethane (TMM) donor with α,β-unsaturated acyl imidazoles is described. A newly designed bisdiamidophosphite ligand derived from (S,S)-trans-1,2-cyclohexanediamine and (2R,4R)-pentanediol has been instrumental f...

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Veröffentlicht in:Journal of the American Chemical Society 2012-07, Vol.134 (28), p.11319-11321
Hauptverfasser: Trost, Barry M, Lam, Tom M
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Lam, Tom M
description A palladium-catalyzed asymmetric [3 + 2] cycloaddition of a vinyl-substituted trimethylenemethane (TMM) donor with α,β-unsaturated acyl imidazoles is described. A newly designed bisdiamidophosphite ligand derived from (S,S)-trans-1,2-cyclohexanediamine and (2R,4R)-pentanediol has been instrumental for the development of this process. This transformation generates tetrasubstituted cyclopentanes bearing three contiguous stereocenters in high yields, with good diastereo- and enantioselectivity.
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title Development of Diamidophosphite Ligands and Their Application to the Palladium-Catalyzed Vinyl-Substituted Trimethylenemethane Asymmetric [3 + 2] Cycloaddition
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