Recent advances in the palladium-catalyzed [3+2] trimethylenemethane cycloaddition (Pd-TMM) have demonstrated the synthesis of tetrahydrofurans, pyrrolidines, and cyclopentanes in great enantioselectivities and yields. The success of this transformation has been due, in large part, to the development of chiral phosphoramidite ligands. We have expanded the scope of these chiral ligands to diimidophosphite ligands such as L1 . Utility of such C2-symmetric bisdiimidophosphite ligands have been differential to the application of substituted-TMM donors to this transformation, forming tetra-substituted cyclopentanes bearing three contiguous stereocenters in high yields, with good diastereo- and enantioselectivities. Herein, we discuss the development of such ligands and their application to the asymmetric TMM cycloaddition. 

Development of bisdiimidophosphite ligands and their application to the asymmetric trimethylenemethane [3+2] cycloaddition

243rd National Meeting (2012)

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