Catalytic Enantioselective Synthesis of Lactams through Formal [4+2] Cycloaddition of Imines with Homophthalic Anhydride

被引：52

作者：

Jarvis, Claire L. ^{[1
]}

Hirschi, Jennifer S. ^{[2
]}

Vetticatt, Mathew J. ^{[2
]}

Seidel, Daniel ^{[1
]}

机构：

[1] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA

[2] Binghamton Univ, Dept Chem, Binghamton, NY 13902 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 10期

基金：

美国国家科学基金会;

关键词：

anion binding; asymmetric catalysis; hydrogen bonding; ion pairing; organocatalysis; STABILIZED BRONSTED ACIDS; ANION-BINDING APPROACH; STEREOSELECTIVE-SYNTHESIS; KINETIC RESOLUTION; DIASTEREOSELECTIVE SYNTHESIS; ASYMMETRIC HYDROGENATION; ABSOLUTE-CONFIGURATIONS; BIOLOGICAL EVALUATION; CYCLIC ANHYDRIDES; ORGANOCATALYSIS;

D O I：

10.1002/anie.201612148

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An amide-thiourea compound, operating through a novel ion pairing mechanism, is an efficient organocatalyst for the asymmetric reaction of homophthalic anhydride with imines. N-aryl and N-alkyl imines readily undergo formal [4+2] cycloaddition to provide lactams with high levels of enantio-and diastereoselectivity. The nature of the key chiral ion pair intermediate was elucidated by DFT calculations.

引用

页码：2670 / 2674

页数：5

共 108 条

[1] Stronger bronsted acids
Akiyama, Takahiko
[J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5744 - 5758
[2] [Anonymous], J CHEM PHYS
[3] [Anonymous], [No title captured]
[4] [Anonymous], 2013, ANGEW CHEM-GER EDIT
[5] Design Strategies for Enhanced Hydrogen- Bond Donor Catalysts
Auvil, Tyler J.
Schafer, Andrew G.
Mattson, Anita E.
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (13) : 2633 - 2646
[6] Recent Advances in Asymmetric Counteranion-directed Catalysis (ACDC)
Avila, Eloah P.
Amarante, Giovanni W.
[J]. CHEMCATCHEM, 2012, 4 (11) : 1713 - 1721
[7] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE
BECKE, AD
[J]. JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) : 5648 - 5652
[8] H-Donor Anion Acceptor Organocatalysis-The Ionic Electrophile Activation Approach
Beckendorf, Stephan
Asmus, Soeren
Mancheno, Olga Garcia
[J]. CHEMCATCHEM, 2012, 4 (07) : 926 - 936
[9] (+)-SJ733, a clinical candidate for malaria that acts through ATP4 to induce rapid host-mediated clearance of Plasmodium
Belen Jimenez-Diaz, Maria
Ebert, Daniel
Salinas, Yandira
Pradhan, Anupam
Lehane, Adele M.
Myrand-Lapierre, Marie-Eve
O'Loughlin, Kathleen G.
Shackleford, David M.
de Almeida, Mariana Justino
Carrillo, Angela K.
Clark, Julie A.
Dennis, Adelaide S. M.
Diep, Jonathon
Deng, Xiaoyan
Duffy, Sandra
Endsley, Aaron N.
Fedewa, Greg
Guiguemde, W. Armand
Gomez, Maria G.
Holbrook, Gloria
Horst, Jeremy
Kim, Charles C.
Liu, Jian
Lee, Marcus C. S.
Matheny, Amy
Santos Martinez, Maria
Miller, Gregory
Rodriguez-Alejandre, Ane
Sanz, Laura
Sigal, Martina
Spillman, Natalie J.
Stein, Philip D.
Wang, Zheng
Zhu, Fangyi
Waterson, David
Knapp, Spencer
Shelat, Anang
Avery, Vicky M.
Fidock, David A.
Gamo, Francisco-Javier
Charman, Susan A.
Mirsalis, Jon C.
Ma, Hongshen
Ferrer, Santiago
Kirk, Kiaran
Angulo-Barturen, Inigo
Kyle, Dennis E.
DeRisi, Joseph L.
Floyd, David M.
Guy, R. Kiplin
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2014, 111 (50) : E5455 - E5462
[10] Enantioselective Acylation of Silyl Ketene Acetals through Fluoride Anion-Binding Catalysis
Birrell, James A.
Desrosiers, Jean-Nicolas
Jacobsen, Eric N.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (35) : 13872 - 13875

← 1 2 3 4 5 6 7 8 9 10 →