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Gold(I)-Catalyzed Enantioselective Synthesis of Pyrazolidines, Isoxazolidines, and Tetrahydrooxazines

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  • We gratefully acknowledge NIHGMS (R01 GM073932-04S1), Bristol-Myers Squibb, and Novartis for funding. R.L.L. thanks Novartis and Eli Lilly and Z.J.W. thanks the Hertz Foundation for graduate fellowships. We thank Dr. Francesco Santoro for preliminary studies on the synthesis of silver biarylsulfonates. We are grateful Johnson Mathey for a generous donation of AuCl3 and to Takasago and Solvias for providing Segphos and MeOBiPhep ligands, respectively.

Abstract

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Au-ff on a trip: Chiral ligands (L*) and chiral anions [(S)-TriPAg] are employed in the gold(I)-catalyzed enantioselective intramolecular additions of hydrazines and hydroxylamines to allenes. These complementary methods allow access to chiral vinyl isoxazolidines, oxazines, and differentially protected pyrazolidines. PNB=para-nitrobenzoyl.

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