Literature DB >> 18722443

Catalytic asymmetric addition of alcohols to imines: enantioselective preparation of chiral N,O-aminals.

Guilong Li1, Frank R Fronczek, Jon C Antilla.   

Abstract

The enantioselective addition of alcohols to imine electrophiles has been shown to proceed in the presence of a catalytic amount of a chiral phosphoric acid catalyst. The reaction allows for the formation of the respective chiral N,O-aminals in excellent yield and enantioselectivity. A total of 11 different alcohols and 11 different imines were successfully used as a clear demonstration of the reaction generality.

Entities:  

Year:  2008        PMID: 18722443     DOI: 10.1021/ja8033334

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


  20 in total

1.  Symmetry in Cascade Chirality-Transfer Processes: A Catalytic Atroposelective Direct Arylation Approach to BINOL Derivatives.

Authors:  Jin-Zheng Wang; Jin Zhou; Chang Xu; Hongbin Sun; László Kürti; Qing-Long Xu
Journal:  J Am Chem Soc       Date:  2016-04-14       Impact factor: 15.419

2.  An asymmetric synthesis of 1,2,4-trioxane anticancer agents via desymmetrization of peroxyquinols through a Brønsted acid catalysis cascade.

Authors:  David M Rubush; Michelle A Morges; Barbara J Rose; Douglas H Thamm; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2012-08-07       Impact factor: 15.419

3.  Enantioselective Synthesis of N,S-Acetals by an Oxidative Pummerer-Type Transformation using Phase-Transfer Catalysis.

Authors:  Souvagya Biswas; Koji Kubota; Manuel Orlandi; Mathias Turberg; Dillon H Miles; Matthew S Sigman; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-12       Impact factor: 15.336

4.  Enantioselective rhodium-catalyzed isomerization of 4-iminocrotonates: asymmetric synthesis of a unique chiral synthon.

Authors:  Wen-Zhen Zhang; John C K Chu; Kevin M Oberg; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2015-01-12       Impact factor: 15.419

5.  Chiral phosphoric acid catalyzed addition of dihydropyrans to N-acyl imines: stereocontrolled access to enantioenriched spirocyclic oxazoletetrahydropyrans with three contiguous stereocenters.

Authors:  Guilong Li; Matthew J Kaplan; Lukasz Wojtas; Jon C Antilla
Journal:  Org Lett       Date:  2010-05-07       Impact factor: 6.005

6.  Stereoselective Synthesis of Dioxolanes and Oxazolidines via a Desymmetrization Acetalization/Michael Cascade.

Authors:  David M Rubush; Tomislav Rovis
Journal:  Synlett       Date:  2014-03       Impact factor: 2.454

7.  A chiral N-phosphinyl phosphoramide: another offspring for the sage phosphoric acid progenitor.

Authors:  Jeffrey N Johnston
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-15       Impact factor: 15.336

8.  Chiral phosphoric acid-catalyzed desymmetrization of meso-aziridines with functionalized mercaptans.

Authors:  Shawn E Larson; Juan C Baso; Guilong Li; Jon C Antilla
Journal:  Org Lett       Date:  2009-11-19       Impact factor: 6.005

9.  Progress toward the total synthesis of psymberin/irciniastatin A.

Authors:  Lauren E Brown; Yakira R Landaverry; James R Davies; Kristin A Milinkevich; Sandra Ast; Joseph S Carlson; Allen G Oliver; Joseph P Konopelski
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

10.  Highly enantioselective hydrogenation of enamides catalyzed by chiral phosphoric acids.

Authors:  Guilong Li; Jon C Antilla
Journal:  Org Lett       Date:  2009-03-05       Impact factor: 6.005

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