Literature DB >> 17192094

Highly enantioselective and diastereoselective 1,3-dipolar cycloaddition reactions between azomethine imines and 3-acryloyl-2-oxazolidinone catalyzed by binaphthyldiimine-Ni(II) complexes.

Hiroyuki Suga1, Akira Funyu, Akikazu Kakehi.   

Abstract

[reaction: see text] We have found the first example of high levels of asymmetric induction (97-74% ee) along with high diastereoselectivity (>99:1-64:36) in dipole-HOMO-/dipolarophile-LUMO-controlled asymmetric 1,3-dipolar cycloaddition reactions between fused azomethine imines and 3-acryloyl-2-oxazolidinone using a chiral BINIM-Ni(II) complex as a chiral Lewis acid catalyst.

Entities:  

Mesh：

Substances：

Year:  2007        PMID： 17192094     DOI： 10.1021/ol062675y

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 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.  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

5.  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

Review 6.  Synthesis of Non-Racemic Pyrazolines and Pyrazolidines by [3+2] Cycloadditions of Azomethine Imines.

Authors:  Franc Požgan; Hamad Al Mamari; Uroš Grošelj; Jurij Svete; Bogdan Štefane
Journal:  Molecules       Date:  2017-12-21       Impact factor: 4.411

7.  Stereoselective Lewis base catalyzed formal 1,3-dipolar cycloaddition of azomethine imines with mixed anhydrides.

Authors:  Lena Hesping; Anup Biswas; Constantin G Daniliuc; Christian Mück-Lichtenfeld; Armido Studer
Journal:  Chem Sci       Date:  2014-11-19       Impact factor: 9.825
  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.