手性金属铑配合物催化的 N，N′-环亚胺亚甲腙不对称 [3 + 2] 环加成反应。
Asymmetric [3 + 2] Cycloaddition Employing N, N'-Cyclic Azomethine Imines Catalyzed by Chiral-at-Metal Rhodium Complex.
机构信息
Key Laboratory of Coal to Ethylene Glycol and Its Related Technology , Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences , 155 Yangqiao Road West , Fuzhou 350002 , China.
University of Chinese Academy of Sciences , Beijing 100049 , China.
出版信息
Org Lett. 2018 Jun 1;20(11):3354-3357. doi: 10.1021/acs.orglett.8b01264. Epub 2018 May 15.
An efficient asymmetric 1,3-dipolar cycloaddition of α,β-unsaturated 2-acyl imidazoles with N, N'-cyclic azomethine imines catalyzed by a chiral-at-metal rhodium complex is reported. The corresponding N, N'-bicyclic pyrazolidine derivatives with three contiguous tertiary stereocenters were obtained in good yields (up to 99%) with excellent stereoselectivities (>20:1 dr and >99% ee). Remarkably, as little as 0.5 mol % of a chiral Rh(III) complex can promote a gram-scale reaction with excellent yield and enantioselectivity.
报道了一种由手性金属铑配合物催化的α,β-不饱和 2-酰基咪唑与 N, N'-环亚甲胺亚胺的高效不对称 1,3-偶极环加成反应。相应的 N, N'-双环吡唑烷衍生物具有三个连续的三级立体中心，收率高（高达 99%），立体选择性好（>20:1 dr 和 >99%ee）。值得注意的是，只需 0.5 mol%的手性 Rh(III)配合物即可促进克级反应，产率和对映选择性优异。
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