Literature DB >> 18816130

Trans-stereoselectivity in the reaction between homophthalic anhydride and imines.

Yosu Vara1, Tamara Bello, Eneko Aldaba, Ana Arrieta, José L Pizarro, María I Arriortua, Xabier Lopez, Fernando P Cossío.   

Abstract

The reaction between homophthalic anhydride and imines in the presence of TiCl4 and diisopropyl ethyl amine is trans-selective. Under these conditions, the reaction using homochiral imines can be highly diastereoselective, thus allowing the synthesis of enantiopure 1,2,3,4-tetrahydro-1-oxoquinoline-4-carboxylic acids.

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Year:  2008        PMID： 18816130     DOI： 10.1021/ol801757r

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


  9 in total

1.  Design, synthesis, and evaluation of dibenzo[c,h][1,6]naphthyridines as topoisomerase I inhibitors and potential anticancer agents.

Authors:  Evgeny Kiselev; Thomas S Dexheimer; Yves Pommier; Mark Cushman
Journal:  J Med Chem       Date:  2010-11-23       Impact factor: 7.446

2.  Formal [4 + 2] cycloaddition of imines with alkoxyisocoumarins.

Authors:  Claire L Jarvis; Neyra M Jemal; Spencer Knapp; Daniel Seidel
Journal:  Org Biomol Chem       Date:  2018-06-13       Impact factor: 3.876

3.  Stereochemistry and Reactivity of the HPA-Imine Mannich Intermediate.

Authors:  Daniel Polyak; Ngan Phung; Jian Liu; Robert Barrows; Thomas J Emge; Spencer Knapp
Journal:  Tetrahedron Lett       Date:  2017-08-31       Impact factor: 2.415

4.  Diastereoselective Base-Catalyzed Formal [4 + 2] Cycloadditions of N-Sulfonyl Imines and Cyclic Anhydrides.

Authors:  Stephen W Laws; Lucas C Moore; Michael J Di Maso; Q Nhu N Nguyen; Dean J Tantillo; Jared T Shaw
Journal:  Org Lett       Date:  2017-05-05       Impact factor: 6.005

5.  Dimerization and comments on the reactivity of homophthalic anhydride.

Authors:  Julia Hong; Zheng Wang; Aaron Levin; Thomas J Emge; David M Floyd; Spencer Knapp
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

6.  Hit-to-Lead Studies for the Antimalarial Tetrahydroisoquinolone Carboxanilides.

Authors:  David M Floyd; Philip Stein; Zheng Wang; Jian Liu; Steve Castro; Julie A Clark; Michele Connelly; Fangyi Zhu; Gloria Holbrook; Amy Matheny; Martina S Sigal; Jaeki Min; Rajkumar Dhinakaran; Senthil Krishnan; Sridevi Bashyum; Spencer Knapp; R Kiplin Guy
Journal:  J Med Chem       Date:  2016-08-25       Impact factor: 7.446

7.  Dibenzo[c,h][1,5]naphthyridinediones as topoisomerase I inhibitors: design, synthesis, and biological evaluation.

Authors:  Evgeny Kiselev; Nicholas Empey; Keli Agama; Yves Pommier; Mark Cushman
Journal:  J Org Chem       Date:  2012-05-15       Impact factor: 4.354

8.  Trifluoroethanol Promoted Castagnoli-Cushman Cycloadditions of Imines with Homophthalic Anhydride.

Authors:  Thibault Bayles; Catherine Guillou
Journal:  Molecules       Date:  2022-01-27       Impact factor: 4.411

9.  N-methylimidazole promotes the reaction of homophthalic anhydride with imines.

Authors:  Jian Liu; Zheng Wang; Aaron Levin; Thomas J Emge; Paul R Rablen; David M Floyd; Spencer Knapp
Journal:  J Org Chem       Date:  2014-07-24       Impact factor: 4.354
  9 in total

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