Literature DB >> 20465280

Unusual reversal of enantioselectivity in the proline-mediated alpha-amination of aldehydes induced by tertiary amine additives.

Donna G Blackmond1, Antonio Moran, Matthew Hughes, Alan Armstrong.   

Abstract

An intriguing reversal in product enantioselectivity accompanied by a change in the kinetic profile is observed in the alpha-amination of aldehydes catalyzed by proline in the presence of organic bases. Implications for the prevailing stereochemical models for proline and related aminocatalytic transformations are discussed.

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Year:  2010        PMID： 20465280     DOI： 10.1021/ja102718x

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


  7 in total

Review 1.  Quantum mechanical investigations of organocatalysis: mechanisms, reactivities, and selectivities.

Authors:  Paul Ha-Yeon Cheong; Claude Y Legault; Joann M Um; Nihan Çelebi-Ölçüm; K N Houk
Journal:  Chem Rev       Date:  2011-06-28       Impact factor: 60.622

Review 2.  Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.

Authors:  Anthony J Metrano; Alex J Chinn; Christopher R Shugrue; Elizabeth A Stone; Byoungmoo Kim; Scott J Miller
Journal:  Chem Rev       Date:  2020-09-24       Impact factor: 60.622

3.  Catalysis of glyceraldehyde synthesis by primary or secondary amino acids under prebiotic conditions as a function of pH.

Authors:  Ronald Breslow; Vijayakumar Ramalingam; Chandrakumar Appayee
Journal:  Orig Life Evol Biosph       Date:  2013-12-18       Impact factor: 1.950

4.  A quantitative approach to nucleophilic organocatalysis.

Authors:  Herbert Mayr; Sami Lakhdar; Biplab Maji; Armin R Ofial
Journal:  Beilstein J Org Chem       Date:  2012-09-05       Impact factor: 2.883

5.  Proline-catalysed amination reactions in cyclic carbonate solvents.

Authors:  Christopher Beattie; Michael North; Pedro Villuendas
Journal:  Molecules       Date:  2011-04-21       Impact factor: 4.411

6.  NMR and Computational Studies on the Reactions of Enamines with Nitroalkenes That May Pass through Cyclobutanes.

Authors:  Alejandro Castro-Alvarez; Héctor Carneros; Jaume Calafat; Anna M Costa; Cristian Marco; Jaume Vilarrasa
Journal:  ACS Omega       Date:  2019-10-25

7.  Enantioselective α-Amination Enabled by a BINAM-Derived Phase-Transfer Catalyst.

Authors:  H M Nelson; J S Patel; H P Shunatona; F D Toste
Journal:  Chem Sci       Date:  2015-01-01       Impact factor: 9.825
  7 in total

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