Literature DB >> 16089444

Kinetic resolutions of azomethine imines via copper-catalyzed [3 + 2] cycloadditions.

Andrés Suárez1, C Wade Downey, Gregory C Fu.   

Abstract

An effective method has been developed for the kinetic resolution of racemic azomethine imines via [3 + 2] cycloadditions with alkynes catalyzed by a chiral copper complex. Efficient kinetic resolution is observed for a variety of N1 and C5 substituents on the dipole, thereby furnishing a wide array of useful enantioenriched azomethine imines, which can readily be transformed into monocyclic and bicyclic pyrazolidinones.

Entities:  

Year:  2005        PMID： 16089444     DOI： 10.1021/ja052876h

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


  14 in total

1.  Discovering New Reactions with N-Heterocyclic Carbene Catalysis.

Authors:  Eric M Phillips; Audrey Chan; Karl A Scheidt
Journal:  Aldrichimica Acta       Date:  2009       Impact factor: 3.667

2.  Highly stereoselective formal [3 + 3] cycloaddition of enals and azomethine imines catalyzed by N-heterocyclic carbenes.

Authors:  Audrey Chan; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2007-04-04       Impact factor: 15.419

3.  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

4.  Highly enantioselective dearomatizing formal [3+3] cycloaddition reactions of N-acyliminopyridinium ylides with electrophilic enol carbene intermediates.

Authors:  Xinfang Xu; Peter Y Zavalij; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-02       Impact factor: 15.336

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.  1,3-Dipolar cycloaddition of arynes with azomethine imines: synthesis of 1,2-dihydropyrazolo[1,2-a]indazol-3(9H)-ones.

Authors:  Feng Shi; Raffaella Mancuso; Richard C Larock
Journal:  Tetrahedron Lett       Date:  2009-07-15       Impact factor: 2.415

7.  Dirhodium(II)-catalyzed formal [3+2+1]-annulation of azomethine imines with two molecules of a diazo ketone.

Authors:  Xinfang Xu; Xichen Xu; Peter Y Zavalij; Michael P Doyle
Journal:  Chem Commun (Camb)       Date:  2013-04-07       Impact factor: 6.222

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.  Gold-catalyzed [3+3]-annulation of azomethine imines with propargyl esters.

Authors:  Nathan D Shapiro; Yun Shi; F Dean Toste
Journal:  J Am Chem Soc       Date:  2009-08-26       Impact factor: 15.419

10.  Crystal structure of (1Z)-1-(4-chloro-benzyl-idene)-5-(4-meth-oxy-phen-yl)-3-oxopyrazolidin-1-ium-2-ide.

Authors:  Peter Mangwala Kimpende; Thi Kieu Oanh Doan; Quoc Trung Vu; Luc Van Meervelt
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-07-19
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