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.

引用

页数：8

共 48 条

[21] Dinuclear zinc-catalyzed enantioselective formal [3+2] cycloaddition of N-2,2,2-trifluoroethylisatin ketimines with low reactivity aurone derivatives
Wang, Rui-Li
Jia, Shi-Kun
Guo, Ya-Jun
Yi, Yang
Hua, Yuan-Zhao
Lu, Hui-Jie
Wang, Min-Can
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (39) : 8492 - 8496
[22] Cu(I)-catalyzed highly exo-selective and enantioselective [3+2] cycloaddition of azomethine ylides with electron-deficient alkenes
Gao, Wenzhong
Raghunath, Malati
Zhang, Xumu
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3060 - U3060
[23] Enantioselective Synthesis of Chiral Imidazolidine Derivatives by Asymmetric Silver/Xing-Phos-Catalyzed Homo-1,3-Dipolar [3+2] Cycloaddition of Azomethine Ylides
Yu, Bo
Bai, Xing-Feng
Lv, Ji-Yuan
Yuan, Yang
Cao, Jian
Zheng, Zhan-Jiang
Xu, Zheng
Cui, Yu-Ming
Yang, Ke-Fang
Xu, Li-Wen
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (20) : 3577 - 3584
[24] Chiral-Boron-Complex-Catalyzed Asymmetric [3+2] Cycloaddition of 2′-Hydroxychalcones with N,N′-Cyclic Azomethine Imines
Chai, Guo-Li
Yao, En-Ze
Liu, Rui-Hao
Chang, Junbiao
ORGANIC LETTERS, 2022, 24 (35) : 6449 - 6454
[25] Chiral Bis(Imidazolidine) Pyridine-Cu Complex-Catalyzed Enantioselective [3+2]-Cycloaddition of Azomethine Imines with Propiolates
Arai, Takayoshi
Ogino, Yuta
MOLECULES, 2012, 17 (05): : 6170 - 6178
[26] First highly regio- and diastereoselective [3+2] cycloaddition of chiral nonracemic Fischer carbene complexes with azomethine ylides:: An enantioselective synthesis of (+)-rolipram
Barluenga, J
Fernández-Rodríguez, MA
Aguilar, E
Fernández-Marí, F
Salinas, A
Olano, B
CHEMISTRY-A EUROPEAN JOURNAL, 2001, 7 (16) : 3533 - 3544
[27] Enantioselective [3+2] cycloaddition of azomethine ylides and aldehydes via Ni/bis(oxazoline)-catalyzed ring opening of N-tosylaziridines through a chirality transfer approach
Wu, Xingxing
Zhou, Wei
Wu, Hai-Hong
Zhang, Junliang
CHEMICAL COMMUNICATIONS, 2017, 53 (41) : 5661 - 5664
[28] Asymmetric [3+2] Cycloaddition Employing N,N'-Cyclic Azomethine lmines Catalyzed by Chiral-at-Metal Rhodium Complex
Gong, Jun
Wan, Qian
Kang, Qiang
ORGANIC LETTERS, 2018, 20 (11) : 3354 - 3357
[29] Chiral-Boron-Complex-Catalyzed Asymmetric [3+2] Cycloaddition of β-Trifluoromethyl α,β-Unsaturated Ketones with N,N′-Cyclic Azomethine Imines
Liu, Rui-Hao
Chai, Guo-Li
Wang, Xiao
Deng, Hong-Yu
Chang, Junbiao
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (23): : 16566 - 16580
[30] Acid-Base Dual-Functional Catalysis by Axially Chiral Guanidine in Enantioselective [3+2] Cycloaddition of Maleate to Schiff Bases as a Precursor of Azomethine Ylides
Nakano, Megumi
Terada, Masahiro
SYNLETT, 2009, (10) : 1670 - 1674

← 1 2 3 4 5 →