Literature DB >> 19788173

Catalytic asymmetric Passerini-type reaction: chiral aluminum-organophosphate-catalyzed enantioselective alpha-addition of isocyanides to aldehydes.

Tao Yue1, Mei-Xiang Wang, De-Xian Wang, Géraldine Masson, Jieping Zhu.   

Abstract

A chiral Lewis acid catalyst was prepared by mixing 2 equiv of chiral binol-derived organophosphoric acid and 1 equiv of Et(2)AlCl. In the presence of a catalytic amount of [4j](2)Al(III)Cl complex (0.05 equiv), reaction between alpha-isocyanoacetamides (2) and aldehydes (3) afforded the corresponding 5-aminooxazoles (1) in good yields and enantioselectivities. Complex [4j](2)Al(III)Cl isolated as a white solid displayed similar reactivity as that prepared in situ.

Entities:  

Mesh：

Substances：

Year:  2009        PMID： 19788173     DOI： 10.1021/jo9017765

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  9 in total

1.  A cooperative N-heterocyclic carbene/chiral phosphate catalysis system for allenolate annulations.

Authors:  Anna Lee; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-04       Impact factor: 15.336

2.  An Efficient Boric Acid Mediated Preparation of α-Hydroxyamides.

Authors:  J Sravan Kumar; Subash C Jonnalagadda; Venkatram R Mereddy
Journal:  Tetrahedron Lett       Date:  2010-02-03       Impact factor: 2.415

3.  Stereoselective Synthesis of Functionalized Bicyclic Scaffolds by Passerini 3-Center-2-Component Reactions of Cyclic Ketoacids.

Authors:  Răzvan C Cioc; Verónica Estévez; Daan J van der Niet; Christophe M L Vande Velde; Nikolaus G Turrini; Mélanie Hall; Kurt Faber; Eelco Ruijter; Romano V A Orru
Journal:  European J Org Chem       Date:  2017-03-08

4.  A N,N'-dioxide/Mg(OTf)2 complex catalyzed enantioselective α-addition of isocyanides to alkylidene malonates.

Authors:  Weiwei Luo; Xiao Yuan; Lili Lin; Pengfei Zhou; Xiaohua Liu; Xiaoming Feng
Journal:  Chem Sci       Date:  2016-04-22       Impact factor: 9.825

5.  Passerini-type reaction of boronic acids enables α-hydroxyketones synthesis.

Authors:  Kai Yang; Feng Zhang; Tongchang Fang; Chaokun Li; Wangyang Li; Qiuling Song
Journal:  Nat Commun       Date:  2021-01-19       Impact factor: 14.919

Review 6.  The 100 facets of the Passerini reaction.

Authors:  Luca Banfi; Andrea Basso; Chiara Lambruschini; Lisa Moni; Renata Riva
Journal:  Chem Sci       Date:  2021-09-30       Impact factor: 9.825

7.  Silica gel-immobilised chiral 1,2-benzenedisulfonimide: a Brønsted acid heterogeneous catalyst for enantioselective multicomponent Passerini reaction.

Authors:  Achille Antenucci; Francesco Marra; Stefano Dughera
Journal:  RSC Adv       Date:  2021-07-29       Impact factor: 4.036

8.  Immobilized Sulfuric Acid on Silica Gel as Highly Efficient and Heterogeneous Catalyst for the One-Pot Synthesis of Novel α-Acyloxycarboxamides in Aqueous Media.

Authors:  Sodeeq Aderotimi Salami; Meloddy Manyeruke; Xavier Siwe-Noundou; Rui Werner Maçedo Krause
Journal:  Int J Mol Sci       Date:  2022-08-23       Impact factor: 6.208

9.  Rh(I)-catalyzed intermolecular hydroacylation: enantioselective cross-coupling of aldehydes and ketoamides.

Authors:  Kevin G M Kou; Diane N Le; Vy M Dong
Journal:  J Am Chem Soc       Date:  2014-06-17       Impact factor: 15.419
  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.