Chiral Bis(imidazolidine)pyridine−Cu(OTf)<sub>2</sub>: Catalytic Asymmetric Endo-Selective [3 + 2] Cycloaddition of Imino Esters with Nitroalkenes
Journal of the American Chemical SocietyPublished 26 March 2010
Takayoshi Arai, Asami Mishiro, Naota Yokoyama, Kuniko Suzuki, Hiroyasu Sato
Citations254
SJR quartileQ1
SJR score5.55
SNIP2.61
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TL;DR
The novel C(2)-symmetric bis(imidazolidine)pyridine (PyBidine) ligand was easily synthesized in a single condensation of 2,6-pyridyl aldehyde and optically active (S,S)-diphenylethylenediamine.
Abstract
The novel C(2)-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 C(2)-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.
Keywords
Chemistry
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