Enantioselective imine reduction catalyzed by imine reductases and artificial metalloenzymes

2014 ◽  
Vol 12 (19) ◽  
pp. 2989-2992 ◽  
Author(s):  
Daniela Gamenara ◽  
Pablo Domínguez de María
Keyword(s):  
Organic Synthesis ◽  
Chiral Amines ◽  
Enantioselective Reduction ◽  
Artificial Metalloenzymes ◽  
Imine Reduction

Adding value to organic synthesis. Novel imine reductases enable the enantioselective reduction of imines to afford chiral amines. Likewise, novel bioinspired artificial metalloenzymes can perform the same reaction as well. Remarkable recent examples are herein discussed.

scholarly journals 2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines

Synlett ◽  
2019 ◽  
Vol 30 (11) ◽  
pp. 1253-1268 ◽  
Author(s):  
Steven J. Malcolmson ◽  
Kangnan Li ◽  
Xinxin Shao
Keyword(s):  
Organic Synthesis ◽  
Metal Species ◽  
Chiral Amines ◽  
Chiral Amine ◽  
Tertiary Alcohols ◽  
Reductive Couplings ◽  
Benzylic Amines ◽  
Important Objective ◽  
New Strategies

The development of new strategies for the preparation of chiral amines is an important objective in organic synthesis. In this Synpacts, we summarize our approach for catalytically accessing nucleophilic aminoalkyl metal species from 2-azadienes, and its application in generating a number of important but elusive chiral amine scaffolds. Reductive couplings with ketones and imines afford 1,2-amino tertiary alcohols and 1,2-diamines, respectively, whereas fluoroarylations of gem-difluoro-2-azadienes deliver α-trifluoromethylated benzylic amines.1 Introduction2 Background: Umpolung Strategies for Preparing Chiral Amines3 Background: 2-Azadienes4 Reductive Couplings of 2-Azadienes5 Fluoroarylations of gem-Difluoro-2-azadienes6 Summary and Outlook

Reduction of Oximes and Hydrazones: Asymmetric and Diastereoselective Approaches

2021 ◽  
Vol 25 ◽  
Author(s):  
João L. P. Ribeiro ◽  
Cláudia Alves ◽  
Ana L. Cardoso ◽  
Susana M. M. Lopes ◽  
Teresa M. V. D. Pinho e Melo
Keyword(s):  
Organic Synthesis ◽  
Asymmetric Reduction ◽  
Building Blocks ◽  
Electrochemical Reactions ◽  
Chiral Amines ◽  
Diastereoselective Reduction ◽  
Metal Catalyzed ◽  
Made In

: The asymmetric reduction of oximes and hydrazones is an attractive and versatile strategy for the synthesis of chiral amines, which are valuable building blocks in organic synthesis. This review summarizes the relevant developments made in the last decade on the enantioselective and diastereoselective reduction of oximes and hydrazones involving metal-catalyzed hydrogenation/hydrogenolysis reactions, hydride donor reactions, and electrochemical reactions.

Kimetic resolution of racemic sulphilimines by enantioselective reduction with arenethiols catalyzed by chiral amines

1983 ◽  
Vol 24 (11) ◽  
pp. 1191-1192 ◽  
Author(s):  
Carlo Dell'Erba ◽  
Marino Novi ◽  
Giacomo Garbarino ◽  
Giancarla Polluzzi Corallo
Keyword(s):  
Chiral Amines ◽  
Enantioselective Reduction

Substrate Scope Evaluation of the Enantioselective Reduction of β-Alkyl-β-arylnitroalkenes by Old Yellow Enzymes 1-3 for Organic Synthesis Applications

ChemCatChem ◽  
2015 ◽  
Vol 8 (3) ◽  
pp. 577-583 ◽  
Author(s):  
Mattia Bertolotti ◽  
Elisabetta Brenna ◽  
Michele Crotti ◽  
Francesco G. Gatti ◽  
Daniela Monti ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Enantioselective Reduction

scholarly journals Characterization of imine reductases in reductive amination for the exploration of structure-activity relationships

2020 ◽  
Vol 6 (21) ◽  
pp. eaay9320 ◽  
Author(s):  
Sarah L. Montgomery ◽  
Ahir Pushpanath ◽  
Rachel S. Heath ◽  
James R. Marshall ◽  
Ulrike Klemstein ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Reductive Amination ◽  
Chiral Amines ◽  
Sequence Motif ◽  
Sequence Structure ◽  
Reaction Conditions ◽  
Rational Engineering ◽  
Structure Activity ◽  
Imine Reduction

Imine reductases (IREDs) have shown great potential as catalysts for the asymmetric synthesis of industrially relevant chiral amines, but a limited understanding of sequence activity relationships makes rational engineering challenging. Here, we describe the characterization of 80 putative and 15 previously described IREDs across 10 different transformations and confirm that reductive amination catalysis is not limited to any particular subgroup or sequence motif. Furthermore, we have identified another dehydrogenase subgroup with chemoselectivity for imine reduction. Enantioselectivities were determined for the reduction of the model substrate 2-phenylpiperideine, and the effect of changing the reaction conditions was also studied for the reductive aminations of 1-indanone, acetophenone, and 4-methoxyphenylacetone. We have performed sequence-structure analysis to help explain clusters in activity across a phylogenetic tree and to inform rational engineering, which, in one case, has conferred a change in chemoselectivity that had not been previously observed.

Sign in / Sign up

Export Citation Format

Share Document