Literature DB >> 25469764

Chiral brønsted Acid-catalyzed stereoselective Mannich-type reaction of azlactones with aldimines.

Eloah P Ávila1, Rodrigo M S Justo1, Vanessa P Gonçalves1, Adriane A Pereira1, Renata Diniz1, Giovanni W Amarante1.   

Abstract

A highly diastereo- and enantioselective Mannich-type reaction of azlactones with aldimines catalyzed by a chiral phosphoric acid is described. Only 3 mol % catalyst was required to prepare the Mannich adducts in good yields with high stereochemical control (up to >19:1 dr, >99:1 er). Moreover, the final product contains two consecutive stereogenic centers, one of which is quaternary.

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Year:  2014        PMID： 25469764     DOI： 10.1021/jo5024975

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


  9 in total

1.  In Situ-Generated Glycinyl Chloroaminals for a One-Pot Synthesis of Non-proteinogenic α-Amino Esters.

Authors:  Shyam S Samanta; Stéphane P Roche
Journal:  J Org Chem       Date:  2017-08-04       Impact factor: 4.354

2.  Catalytic, Enantioselective α-Alkylation of Azlactones with Nonconjugated Alkenes by Directed Nucleopalladation.

Authors:  Sri Krishna Nimmagadda; Mingyu Liu; Malkanthi K Karunananda; De-Wei Gao; Omar Apolinar; Jason S Chen; Peng Liu; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-27       Impact factor: 15.336

3.  A Brønsted base-promoted diastereoselective dimerization of azlactones.

Authors:  Danielle L J Pinheiro; Gabriel M F Batista; Pedro P de Castro; Leonã S Flores; Gustavo F S Andrade; Giovanni W Amarante
Journal:  Beilstein J Org Chem       Date:  2017-12-13       Impact factor: 2.883

4.  Selecting Chiral BINOL-Derived Phosphoric Acid Catalysts: General Model To Identify Steric Features Essential for Enantioselectivity.

Authors:  Jolene P Reid; Jonathan M Goodman
Journal:  Chemistry       Date:  2017-09-14       Impact factor: 5.236

5.  Theoretical Study on the Epimerization of Azlactone Rings: Keto-Enol Tautomerism or Base-Mediated Racemization?

Authors:  Pedro P de Castro; Gabriel M F Batista; Hélio F Dos Santos; Giovanni W Amarante
Journal:  ACS Omega       Date:  2018-03-26

6.  Brønsted acid catalysis - the effect of 3,3'-substituents on the structural space and the stabilization of imine/phosphoric acid complexes.

Authors:  Maxime Melikian; Johannes Gramüller; Johnny Hioe; Julian Greindl; Ruth M Gschwind
Journal:  Chem Sci       Date:  2019-04-08       Impact factor: 9.825

7.  Brønsted Acid-Catalyzed Epimerization-Free Preparation of Dual-Protected Amino Acid Derivatives.

Authors:  Pedro P de Castro; Isabela M R Rimulo; Angelina M de Almeida; Renata Diniz; Giovanni W Amarante
Journal:  ACS Omega       Date:  2017-06-27

8.  A Brønsted Acid-Catalyzed Multicomponent Reaction for the Synthesis of Highly Functionalized γ-Lactam Derivatives.

Authors:  Xabier Del Corte; Edorta Martinez de Marigorta; Francisco Palacios; Javier Vicario
Journal:  Molecules       Date:  2019-08-14       Impact factor: 4.411

9.  Internal acidity scale and reactivity evaluation of chiral phosphoric acids with different 3,3'-substituents in Brønsted acid catalysis.

Authors:  Kerstin Rothermel; Maxime Melikian; Johnny Hioe; Julian Greindl; Johannes Gramüller; Matej Žabka; Nils Sorgenfrei; Thomas Hausler; Fabio Morana; Ruth M Gschwind
Journal:  Chem Sci       Date:  2019-09-06       Impact factor: 9.825
  9 in total

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