DBU-Promoted Dynamic Kinetic Resolution in Rh-Catalyzed Asymmetric Transfer Hydrogenation of 5-Alkyl Cyclic Sulfamidate Imines: Stereoselective Synthesis of Functionalized 1,2-Amino Alcohols

2018 ◽  
Vol 83 (19) ◽  
pp. 11987-11999 ◽  
Author(s):  
Hyeong Rae Kim ◽  
Raghavendra Achary ◽  
Hyeon-Kyu Lee
Keyword(s):  
Kinetic Resolution ◽  
Stereoselective Synthesis ◽  
Amino Alcohols ◽  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Dynamic Kinetic Resolution

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%).

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