Regioselectivity Change in the Organocatalytic Enantioselective (3+2) Cycloaddition with Nitrones through Cooperative Hydrogen-Bonding Catalysis/Iminium Activation

被引：16

作者：

Prieto, Liher ^{[1
]}

Juste-Navarro, Veronica ^{[2
]}

Uria, Uxue ^{[1
]}

Delso, Ignacio ^{[2
]}

Reyes, Efraim ^{[1
]}

Tejero, Tomas ^{[2
]}

Carrillo, Luisa ^{[1
]}

Merino, Pedro ^{[2
]}

Vicario, Jose L. ^{[1
]}

机构：

[1] Univ Basque Country UPV EHU, Dept Organ Chem 2, POB 644, Bilbao 48080, Spain

[2] Univ Zaragoza, CSIC, ISQCH, Lab Sintesis Asimetr, Campus San Francisco, Zaragoza 5009, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 12期

关键词：

asymmetric catalysis; cycloaddition; nitrones; organocatalysis; pyrrolidines; 1,3-DIPOLAR CYCLOADDITIONS; AZOMETHINE YLIDES; ASYMMETRIC-SYNTHESIS; ORGANIC CATALYSIS; ALDEHYDES; STRATEGIES; REACTIVITY; PYRROLIDINES; ETHERS;

D O I：

10.1002/chem.201605350

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of nitrones with enals through iminium activation can be modulated by using cooperative hydrogen-bonding catalysis to induce the participation of a nitrone ylide (C-N-C) instead of the classical C-N-O dipole. As a consequence, N-hydroxypyrrolidines are obtained, rather than the expected isoxazolidines. The reaction proceeds smoothly and high enantioselectivities are observed in all cases. By using the appropriate substrate, polysubstituted pyrrolidines incorporating quaternary stereocenters can be efficiently prepared.

引用

页码：2764 / 2768

页数：5

共 47 条

[31] Highly Enantioselective Organocatalytic Michael Addition/Cyclization Cascade Reaction of Ylideneoxindoles with Isothiocyanato Oxindoles: A Formal [3+2] Cycloaddition Approach to Optically Active Bispirooxindole Derivatives
Tan, Fen
Cheng, Hong-Gang
Feng, Bin
Zou, You-Quan
Duan, Shu-Wen
Chen, Jia-Rong
Xiao, Wen-Jing
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (11) : 2071 - 2075
[32] Enantioselective (3+2)-Annulation of β-Keto Esters with Azoalkenes towards Bicyclic Dihydropyrroles via Cooperative Palladium and Brønsted Acid Catalysis
Friedmann, Till
Mireles-Chavez, Daniel A.
Walter, Frederik L.
Schneider, Christoph
SYNLETT, 2024, 35 (09) : 997 - 1000
[33] Enantioselective catalysis of the hetero-Diels-Alder reaction between Brassard's diene and aldehydes by hydrogen-bonding activation:: A one-step synthesis of (S)-(+)-Dihydrokawain
Du, HF
Zhao, DB
Ding, KL
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (23) : 5964 - 5970
[34] Understanding the Origin of the Regioselectivity in Non-Polar [3+2] Cycloaddition Reactions through the Molecular Electron Density Theory
Domingo, Luis R.
Gutierrez, Mar Rios
Soriano, Jorge Castellanos
ORGANICS, 2020, 1 (01): : 19 - 35
[35] 4-Alkenyl-5H-1,2,3-oxathiazole 2,2-dioxides in catalytic and enantioselective [4+2] cycloaddition through iminium activation. Straightforward access to the trans-decaline framework and to densely functionalized cyclohexanes
Riano, Iker
Uria, Uxue
Carrillo, Luisa
Reyes, Efraim
Vicario, Jose L.
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (03): : 206 - 210
[36] Chiral Bronsted Base Activation of Donor-Acceptor Cyclopropanes toward Diastereo- and Enantioselective [3+2] Cycloaddition with Isatin-Derived Ketimines
Yu, Zhe-Jia
Yan, Shuang
Zhao, Xiao-Li
Zhang, Jun
Zhao, Mei-Xin
JOURNAL OF ORGANIC CHEMISTRY, 2024, : 8691 - 8705
[37] Enantioselective Synthesis of Spirocyclopentane Oxindoles Bearing Five Consecutive Stereocenters through Secondary Amine-Catalyzed [3+2] Cycloaddition
Zhou, Jing-Wei
Chen, Ben-Hong
Zhang, Feng-Hua
Xue, Jing
He, Xiang-Hong
Peng, Cheng
Huang, Wei
Zhao, Qian
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (20)
[38] Diastereo- and Enantioselective Synthesis of Chiral Pyrrolidine-Fused Spirooxindoles via Organocatalytic [3+2] 1,3-Dipolar Cycloaddition of Azomethine Ylides with Maleimides
Zhao, Hong-Wu
Yang, Zhao
Meng, Wei
Tian, Ting
Li, Bo
Song, Xiu-Qing
Chen, Xiao-Qin
Pang, Hai-Liang
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (11) : 2492 - 2502
[39] Enantioselective Synthesis of Highly Functionalized Dihydrofurans through Copper-Catalyzed Asymmetric Formal [3+2] Cycloaddition of β-Ketoesters with Propargylic Esters
Zhu, Fu-Lin
Wang, Ya-Hui
Zhang, De-Yang
Xu, Jie
Hu, Xiang-Ping
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (38) : 10223 - 10227
[40] Palladium-Catalyzed Diastereo- and Enantioselective Synthesis of Substituted Cyclopentanes through a Dynamic Kinetic Asymmetric Formal [3+2]-Cycloaddition of Vinyl Cyclopropanes and Alkylidene Azlactones
Trost, Barry M.
Morris, Patrick J.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (27) : 6167 - 6170

← 1 2 3 4 5 →