ChemInform Abstract: SYNTHESIS OF CHIRAL DEPSIPEPTIDE BUILDING BLOCK BY THE ASYMMETRIC REDUCTION OF N-(α-KETOACYL)-α-AMINO ESTERS

1981 ◽  
Vol 12 (49) ◽  
Author(s):  
I. OJIMA ◽  
T. TANAKA ◽  
T. KOGURE
Keyword(s):  
Building Block ◽  
Asymmetric Reduction ◽  
Amino Esters

SYNTHESIS OF CHIRAL DEPSIPEPTIDE BUILDING BLOCK BY THE ASYMMETRIC REDUCTION OFN-(α-KETOACYL)-α-AMINO ESTERS

1981 ◽  
Vol 10 (6) ◽  
pp. 823-826 ◽  
Author(s):  
Iwao Ojima ◽  
Toshiyuki Tanaka ◽  
Tetsuo Kogure
Keyword(s):  
Building Block ◽  
Asymmetric Reduction ◽  
Amino Esters

Chiral Phosphinyl Enamines and Their Asymmetric Reduction through Group-Assisted Purification Chemistry Leading to Enantiopure β-Amino Esters/Amides

Synlett ◽  
2017 ◽  
Vol 28 (18) ◽  
pp. 2483-2488 ◽  
Author(s):  
Bo Jiang ◽  
Guigen Li ◽  
Shuo Qiao ◽  
Jianbin Wu ◽  
Junming Mo ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Efficient Method ◽  
Asymmetric Reduction ◽  
Sodium Cyanoborohydride ◽  
Amino Esters

A series of new chiral N-phosphinyl β-enamino esters and amides were successfully prepared with excellent Z-stereoselectivity (Z/E > 99:1 in nearly all cases). Group-assisted purification chemistry proved to be an efficient method for the asymmetric reduction of the resulting β-enamino esters/amides to give enantiopure β-amino esters/amides. The asymmetric reduction can be controlled efficiently by using a combination of sodium cyanoborohydride and acetic acid.

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