Concepedia

Catalytic Enantioselective 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with α,β-Unsaturated Aldehydes

Takuya Hashimoto, Yuko Maeda, M. Omote, Hiroki Nakatsu, Keiji Maruoka

Journal of the American Chemical Society · 2010 · 178 citations · 32 references

DOI

Concepts

Abstract

A yet-unexploited class of azomethine imines, C,N-cyclic azomethine imines, could be successfully employed in highly enantioselective 1,3-dipolar cycloaddition with enals catalyzed by titanium-BINOLate to give pharmaceutically attractive tetrahydroisoquinoline and piperidine motifs.

References

32

Asymmetric 1,3-dipolar cycloadditions

Hélène Pellissier · Tetrahedron · 2007 · 637 citations

Recent Advances in the Total Synthesis of Piperidine and Pyrrolidine Natural Alkaloids with Ring‐Closing Metathesis as a Key Step

François‐Xavier Felpin, Jacques Lebreton · European Journal of Organic Chemistry · 2003 · 436 citations

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A New Copper-Catalyzed [3 + 2] Cycloaddition:  Enantioselective Coupling of Terminal Alkynes with Azomethine Imines To Generate Five-Membered Nitrogen Heterocycles

Ryo Shintani, Gregory C. Fu · Journal of the American Chemical Society · 2003 · 330 citations

, , +16

Asymmetric routes to substituted piperidines

Patrick D. Bailey, Paula A. Millwood, Peter D. Smith · Chemical Communications · 1998 · 328 citations

, , +12

Highly Stereoselective Formal [3 + 3] Cycloaddition of Enals and Azomethine Imines Catalyzed by <i>N</i>-Heterocyclic Carbenes

Audrey Chan, Karl A. Scheidt · Journal of the American Chemical Society · 2007 · 320 citations · Full text

, , +15