Literature DB >> 20199072

Catalytic enantioselective 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines with alpha,beta-unsaturated aldehydes.

Takuya Hashimoto1, Yuko Maeda, Masato Omote, Hiroki Nakatsu, Keiji Maruoka.   

Abstract

A yet-unexploited class of azomethine imines, C,N-cyclic azomethine imines, could be successfully employed in highly enantioselective 1,3-dipolar cycloaddition with enals catalyzed by titanium-BINOLate to give pharmaceutically attractive tetrahydroisoquinoline and piperidine motifs.

Entities:  

Year:  2010        PMID： 20199072     DOI： 10.1021/ja100787a

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  15 in total

1.  Synthesis of macrocyclic tetrazoles for rapid photoinduced bioorthogonal 1,3-dipolar cycloaddition reactions.

Authors:  Zhipeng Yu; Reyna K V Lim; Qing Lin
Journal:  Chemistry       Date:  2010-12-03       Impact factor: 5.236

2.  Phosphine-catalyzed annulations of azomethine imines: allene-dependent [3 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] pathways.

Authors:  Risong Na; Chengfeng Jing; Qihai Xu; Hui Jiang; Xi Wu; Jiayan Shi; Jiangchun Zhong; Min Wang; Diego Benitez; Ekaterina Tkatchouk; William A Goddard; Hongchao Guo; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2011-08-03       Impact factor: 15.419

3.  Enantioselective approach to quinolizidines: total synthesis of cermizine D and formal syntheses of senepodine G and cermizine C.

Authors:  Nagarathanam Veerasamy; Erik C Carlson; Nathan D Collett; Mrinmoy Saha; Rich G Carter
Journal:  J Org Chem       Date:  2013-04-29       Impact factor: 4.354

4.  One-pot synthesis of novel 1-(1H-tetrazol-5-yl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine derivatives via an Ugi-azide 4CR process.

Authors:  Mehdi Ghandi; Saleh Salahi; Abuzar Taheri; Alireza Abbasi
Journal:  Mol Divers       Date:  2017-12-11       Impact factor: 2.943

5.  Phosphine-Catalyzed [3+2] and [4+3]Annulation Reactions of C,N-Cyclic Azomethine Imines with Allenoates.

Authors:  Chengfeng Jing; Risong Na; Bo Wang; Honglei Liu; Lei Zhang; Jun Liu; Min Wang; Jiangchun Zhong; Ohyun Kwon; Hongchao Guo
Journal:  Adv Synth Catal       Date:  2012-04-26       Impact factor: 5.837

6.  Generation and exploitation of acyclic azomethine imines in chiral Brønsted acid catalysis.

Authors:  Takuya Hashimoto; Hidenori Kimura; Yu Kawamata; Keiji Maruoka
Journal:  Nat Chem       Date:  2011-07-22       Impact factor: 24.427

7.  Intramolecular polar [4(⊕)+2] cycloadditions of aryl-1-aza-2-azoniaallene salts: unprecedented reactivity leading to polycyclic protonated azomethine imines.

Authors:  Daniel A Bercovici; Jodi M Ogilvie; Nikolay Tsvetkov; Matthias Brewer
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-11       Impact factor: 15.336

8.  Highly selective catalyst-dependent competitive 1,2-C→C, -O→C, and -N→C migrations from β-methylene-β-silyloxy-β-amido-α-diazoacetates.

Authors:  Xichen Xu; Yu Qian; Peter Y Zavalij; Michael P Doyle
Journal:  J Am Chem Soc       Date:  2013-01-17       Impact factor: 15.419

9.  Bicyclic pyrazolidinone derivatives from diastereoselective catalytic [3 + 3]-cycloaddition reactions of enoldiazoacetates with azomethine imines.

Authors:  Yu Qian; Peter J Zavalij; Wenhao Hu; Michael P Doyle
Journal:  Org Lett       Date:  2013-03-11       Impact factor: 6.005

10.  [3 + 2]-Cycloadditions of Azomethine Imines and Ynolates.

Authors:  Sarah E Winterton; Joseph M Ready
Journal:  Org Lett       Date:  2016-05-24       Impact factor: 6.005
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