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

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Chiral Bis(imidazolidine)pyridine−Cu(OTf)2: Catalytic Asymmetric Endo-Selective [3 + 2] Cycloaddition of Imino Esters with Nitroalkenes
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2010-04-21 , DOI: 10.1021/ja100265j
Takayoshi Arai ₁ , Asami Mishiro ₁ , Naota Yokoyama ₁ , Kuniko Suzuki ₁ , Hiroyasu Sato ₁

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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.

中文翻译：

手性双(咪唑烷)吡啶-Cu(OTf)2：亚氨基酯与硝基烯烃的催化不对称内选择性[3 + 2]环加成

新型 C(2)-对称双 (咪唑烷) 吡啶 (PyBidine) 配体很容易在 2,6-吡啶醛和旋光 (S,S)-二苯基乙二胺的单次缩合中合成。在 C(2)-对称 PyBidine-Cu(OTf)(2) 复合物中，咪唑烷环充当“手性围栏”来屏蔽第一和第三象限。使用 PyBidine-Cu(OTf)(2) 配合物作为催化剂可以实现亚氨基酯和硝基烯烃的高度内选择性反应，得到高达 99% ee 的加合物。

更新日期：2010-04-21

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