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Chiral Bis(imidazolidine)pyridine−Cu(OTf)2: Catalytic Asymmetric Endo-Selective [3 + 2] Cycloaddition of Imino Esters with Nitroalkenes

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Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522, Japan, and Application Laboratory, Rigaku Corporation, Akishima, Tokyo 196-8666, Japan
†Chiba University.
‡Rigaku Corporation.
Cite this: J. Am. Chem. Soc. 2010, 132, 15, 5338–5339
Publication Date (Web):March 26, 2010
Copyright © 2010 American Chemical Society

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    The novel C2-symmetric bis(imidazolidine)pyridine (PyBidine) ligand was easily synthesized in a single condensation of 2,6-pyridyl aldehyde and optically active (S,S)-diphenylethylenediamine. In the C2-symmetric PyBidine−Cu(OTf)2 complex, imidazolidine rings act as “chiral fences” to shield the first and third quadrants. Use of the PyBidine−Cu(OTf)2 complex as a catalyst enabled the highly endo-selective reaction of imino esters and nitroalkenes to give the adducts in up to 99% ee.

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