Zinc-Catalyzed Enantioselective [3+2] Cycloaddition of Azomethine Ylides Using Planar Chiral [2.2]Paracyclophane-Imidazoline N,O-ligands

被引：14
|
作者：
Kumar, Sundaravel Vivek [1 ]
Guiry, Patrick J. [1 ]
机构：
[1] Univ Coll Dublin UCD, Ctr Synth & Chem Biol CSCB, Sch Chem, Dublin 4, Ireland
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2022年 / 61卷 / 33期
基金：
爱尔兰科学基金会;
关键词：
Asymmetric Catalysis; Cycloaddition; Cyclophanes; Planar Chiral; Zinc Catalysis; OXAZOLINE-CONTAINING LIGANDS; ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION; CONJUGATE ADDITION; DERIVATIVES; FUNCTIONALIZATION; DIETHYLZINC; ALDEHYDES; IMINES; ETHYL;
D O I：
10.1002/anie.202205516
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We present a facile synthetic route toward a novel series of imidazolinyl-[2.2]paracyclophanol (UCD-Imphanol) ligands possessing central and planar chirality. Both sets of diastereomeric ligands were successfully purified by column chromatography. The preliminary application of this family of ligands showed excellent activities in the asymmetric Zn-catalyzed azomethine ylide cycloaddition. Enantioenriched pyrrolidines, in a substrate scope of 20 examples, were accessed in high levels of endo/exo ratios (up to >99/1) and enantioselectivities (up to >99 % ee) with excellent yields (up to 99 %) by using (S,S,S-P)-UCD-Imphanol/(S,S,R-P)-UCD-Imphanol, respectively.
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页数：8
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