Literature DB >> 19249818

Mechanism of BINOL--phosphoric acid-catalyzed strecker reaction of benzyl imines.

Luis Simón1, Jonathan M Goodman.   

Abstract

The mechanism and the origin of the selectivity for the BINOL-phosphoric acid-catalyzed Strecker reaction on N-benzyl imines has been investigated by theoretical methods and compared with earlier studies of N-aryl imines. ONIOM calculations show that the reverse in selectivity which is observed experimentally is not due to differences in the steric bulk of aryl and benzyl groups, but rather because of a switch from a preference for a Z imine to an E imine in the transition state of benzaldehyde-derived imines. The calculations predict this change will not be present for imines formed from acetophenone.

Entities:  

Year:  2009        PMID： 19249818     DOI： 10.1021/ja808715j

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


  10 in total

1.  Origins of stereoselectivities in chiral phosphoric acid catalyzed allylborations and propargylations of aldehydes.

Authors:  Hao Wang; Pankaj Jain; Jon C Antilla; K N Houk
Journal:  J Org Chem       Date:  2013-01-18       Impact factor: 4.354

2.  Asymmetric catalytic N-phosphonyl imine chemistry: the use of primary free amino acids and Et2AlCN for asymmetric catalytic Strecker reaction.

Authors:  Parminder Kaur; Suresh Pindi; Walter Wever; Trideep Rajale; Guigen Li
Journal:  J Org Chem       Date:  2010-08-06       Impact factor: 4.354

3.  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

4.  Catalytic asymmetric aza-Darzens reaction with a vaulted biphenanthrol magnesium phosphate salt.

Authors:  Shawn E Larson; Guilong Li; Gerald B Rowland; Denise Junge; Rongcai Huang; H Lee Woodcock; Jon C Antilla
Journal:  Org Lett       Date:  2011-04-05       Impact factor: 6.005

5.  Mechanism of amido-thiourea catalyzed enantioselective imine hydrocyanation: transition state stabilization via multiple non-covalent interactions.

Authors:  Stephan J Zuend; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2009-10-28       Impact factor: 15.419

6.  A truly green synthesis of α-aminonitriles via Strecker reaction.

Authors:  Debasish Bandyopadhyay; Juliana M Velazquez; Bimal K Banik
Journal:  Org Med Chem Lett       Date:  2011-10-04

7.  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

8.  Ternary complexes of chiral disulfonimides in transfer-hydrogenation of imines: the relevance of late intermediates in ion pair catalysis.

Authors:  Matej Žabka; Ruth M Gschwind
Journal:  Chem Sci       Date:  2021-11-17       Impact factor: 9.825

9.  Asymmetric Synthesis of Heterocyclic Chloroamines and Aziridines by Enantioselective Protonation of Catalytically Generated Enamines.

Authors:  Liam A McLean; Matthew W Ashford; James W B Fyfe; Alexandra M Z Slawin; Andrew G Leach; Allan J B Watson
Journal:  Chemistry       Date:  2022-02-23       Impact factor: 5.020

10.  Catalytic Enantioselective Synthesis of Heterocyclic Vicinal Fluoroamines by Using Asymmetric Protonation: Method Development and Mechanistic Study.

Authors:  Matthew W Ashford; Chao Xu; John J Molloy; Cameron Carpenter-Warren; Alexandra M Z Slawin; Andrew G Leach; Allan J B Watson
Journal:  Chemistry       Date:  2020-08-18       Impact factor: 5.236
  10 in total

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