Rhodium-Catalyzed anti and syn Enantio- and Diastereoselective Transfer Hydrogenation of α-Amino β-Keto Ester Hydrochlorides through Dynamic Kinetic Resolution

Synthesis ◽  
2016 ◽  
Vol 48 (19) ◽  
pp. 3357-3363 ◽  
Author(s):  
Quentin Llopis ◽  
Charlène Férard ◽  
Gérard Guillamot ◽  
Phannarath Phansavath ◽  
Virginie Ratovelomanana-Vidal
Keyword(s):  
Formic Acid ◽  
Kinetic Resolution ◽  
Amino Alcohols ◽  
Hydrogen Donor ◽  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Dynamic Kinetic Resolution ◽  
Keto Ester ◽  
Catalytic Asymmetric ◽  
Donor Source

A mild catalytic asymmetric transfer hydrogenation of a series of α-amino β-keto ester hydrochlorides catalyzed by a rhodium(III) complex is reported. The use of the formic acid/triethylamine system as the hydrogen donor source provided the corresponding anti and syn amino alcohols with complete conversions, fair diastereoselectivities (up to 97:3 dr), and high enantioselectivities (ee up to >99%).

Asymmetric transfer hydrogenation of α-amino β-keto ester hydrochlorides through dynamic kinetic resolution

RSC Advances ◽  
2015 ◽  
Vol 5 (70) ◽  
pp. 56815-56819 ◽  
Author(s):  
Pierre-Georges Echeverria ◽  
Johan Cornil ◽  
Charlène Férard ◽  
Amandine Guérinot ◽  
Janine Cossy ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Dynamic Kinetic Resolution ◽  
Keto Ester

The development of Ru-catalyzed asymmetric transfer hydrogenation of α-amino β-keto ester hydrochlorides is described.

ChemInform Abstract: Asymmetric Transfer Hydrogenation of α-Amino β-Keto Ester Hydrochlorides Through Dynamic Kinetic Resolution.

ChemInform ◽  
2015 ◽  
Vol 46 (46) ◽  
pp. no-no
Author(s):  
Pierre-Georges Echeverria ◽  
Johan Cornil ◽  
Charlene Ferard ◽  
Amandine Guerinot ◽  
Janine Cossy ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Dynamic Kinetic Resolution ◽  
Keto Ester

Catalytic asymmetric transfer hydrogenation/dynamic kinetic resolution: an efficient synthesis of florfenicol

Tetrahedron ◽  
2016 ◽  
Vol 72 (14) ◽  
pp. 1787-1793 ◽  
Author(s):  
Xinlong Wang ◽  
Lingjun Xu ◽  
Lingjie Yan ◽  
Haifeng Wang ◽  
Sheng Han ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Transfer Hydrogenation ◽  
Efficient Synthesis ◽  
Asymmetric Transfer Hydrogenation ◽  
Dynamic Kinetic Resolution ◽  
Catalytic Asymmetric

scholarly journals trans-Diastereoselective Ru(II)-Catalyzed Asymmetric Transfer Hydrogenation of α-Acetamido Benzocyclic Ketones via Dynamic Kinetic Resolution

2019 ◽  
Vol 21 (10) ◽  
pp. 3644-3648 ◽  
Author(s):  
Andrej Emanuel Cotman ◽  
Matic Lozinšek ◽  
Baifan Wang ◽  
Michel Stephan ◽  
Barbara Mohar
Keyword(s):  
Kinetic Resolution ◽  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Dynamic Kinetic Resolution

A new cost-effective Ru-chloramphenicol base derivative catalyst for the asymmetric transfer hydrogenation/dynamic kinetic resolution of N-Boc α-amino-β-ketoesters and its application to the synthesis of the chiral core of vancomycin

RSC Advances ◽  
2016 ◽  
Vol 6 (44) ◽  
pp. 37701-37709 ◽  
Author(s):  
Xinlong Wang ◽  
Lingjun Xu ◽  
Fangjun Xiong ◽  
Yan Wu ◽  
Fener Chen
Keyword(s):  
Asymmetric Synthesis ◽  
Kinetic Resolution ◽  
Cost Effective ◽  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Dynamic Kinetic Resolution ◽  
Amino Esters ◽  
Base Derivative

Herein we describe the application of Ru-chloramphenicol base complexes catalyzed highly diastereo- and enantioselective transfer hydrogenation of N-Boc α-amino-β-ketoesters for the asymmetric synthesis of anti-N-Boc-β-hydroxy-α-amino esters.

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