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 50 条

[1] Formal [4+2] cycloaddition of imines with alkoxyisocoumarins
Jarvis, Claire L.
Jemal, Neyra M.
Knapp, Spencer
Seidel, Daniel
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (23) : 4231 - 4235
[2] Catalytic Enantioselective Synthesis of Guvacine Derivatives through [4+2] Annulations of Imines with α-Methylallenoates
Xu, Qihai
Dupper, Nathan J.
Smaligo, Andrew J.
Fan, Yi Chiao
Cai, Lingchao
Wang, Zhiming
Langenbacher, Adam D.
Chen, Jau-Nian
Kwon, Ohyun
ORGANIC LETTERS, 2018, 20 (19) : 6089 - 6093
[3] Highly Enantioselective Catalytic Kinetic Resolution of α-Branched Aldehydes through Formal Cycloaddition with Homophthalic Anhydrides
Farid, Umar
Aiello, Maria Luisa
Connon, Stephen J.
CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (43) : 10074 - 10079
[4] Unexpected formal [4+2]-cycloaddition of chalcone imines and homophthalic anhydrides: preparation of dihydropyridin-2(1H)-ones
Guranova, Natalia
Golubev, Pavel
Bakulina, Olga
Dar'in, Dmitry
Kantin, Grigory
Krasavin, Mikhail
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (17) : 3829 - 3833
[5] Tetrahydroquinolines and Benzazepines through Catalytic Diastereoselective Formal [4+2]-Cycloaddition Reactions between Donor-Acceptor Cyclopropenes and Imines
Truong, Phong M.
Mandler, Michael D.
Zavalij, Peter Y.
Doyle, Michael P.
ORGANIC LETTERS, 2013, 15 (13) : 3278 - 3281
[6] Enantioselective Synthesis of N-PMP-1,2-dihydropyridines via Formal [4+2] Cycloaddition between Aqueous Glutaraldehyde and Imines
Ramaraju, Panduga
Mir, Nisar A.
Singh, Deepika
Gupta, Vivek K.
Kant, Rajni
Kumar, Indresh
ORGANIC LETTERS, 2015, 17 (22) : 5582 - 5585
[7] Enantioselective Rhodium-Catalyzed [4+2] Cycloaddition of α,β-Unsaturated Imines and Isocyanates
Oberg, Kevin M.
Rovis, Tomislav
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (13) : 4785 - 4787
[8] Chiral Phosphoric Acid Catalyzed Enantioselective [4+2] Cycloaddition Reaction of α-Fluorostyrenes with Imines
Kikuchi, Jun
Ye, Haiting
Terada, Masahiro
ORGANIC LETTERS, 2020, 22 (22) : 8957 - 8961
[9] Catalytic Ynone-Amidine Formal [4+2]-Cycloaddition for the Regioselective Synthesis of Tricyclic Azepines
Reddy, T. Prabhakar
Gujral, Jagjeet
Roy, Pritam
Ramachary, Dhevalapally B.
ORGANIC LETTERS, 2020, 22 (24) : 9653 - 9657
[10] Catalytic asymmetric synthesis of piperidine derivatives through the [4+2] annulation of imines with allenes
Wurz, RP
Fu, GC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (35) : 12234 - 12235

← 1 2 3 4 5 →