An Efficient Method for Catalytic Asymmetric Reduction of Diketones and Application of Synthesis to Chiral 2,5-Diphenylpyrrolidine and 2,5-Diphenylthiolane

2006 ◽  
Vol 24 (10) ◽  
pp. 1402-1405 ◽  
Author(s):  
Xiang Li ◽  
Gang Zhao ◽  
Wei-Guo Cao
Keyword(s):  
Efficient Method ◽  
Asymmetric Reduction ◽  
Catalytic Asymmetric

scholarly journals Asymmetric Synthetic Strategies of (R)-(–)-Baclofen: An Antispastic Drug

Synthesis ◽  
2017 ◽  
Vol 50 (02) ◽  
pp. 211-226 ◽  
Author(s):  
Perla Ramesh ◽  
Devatha Suman ◽  
Koti Reddy
Keyword(s):  
Asymmetric Reduction ◽  
Asymmetric Hydrogenation ◽  
Asymmetric Aldol ◽  
Asymmetric Michael Addition ◽  
Chemical Resolution ◽  
Enzymatic Desymmetrization ◽  
Catalytic Asymmetric ◽  
Aldol Addition ◽  
Synthetic Approaches ◽  
Catalytic Asymmetric Hydrogenation

Baclofen is an antispastic drug used as a muscle relaxant in the treatment of the paroxysmal pain of trigeminal neuralgia, spasticity of the spinal cord and cerebral origin. Baclofen resides biological activity exclusively in its (R)-(–)-enantiomer. In this review, various asymmetric synthetic strategies for (R)-(–)-baclofen are described.1 Introduction2 Resolution Synthetic Approaches2.1 Chemical Resolution2.2 Biocatalytic Resolution3 Asymmetric Desymmetrization3.1 Catalytic Enantioselective Desymmetrization3.2 Enzymatic Desymmetrization4 Chiral Auxiliary Induced Asymmetric Synthesis4.1 Asymmetric Michael Addition4.2 Asymmetric Aldol Addition4.3 Asymmetric Nucleophilic Substitution5 Asymmetric Reduction5.1 Catalytic Asymmetric Hydrogenation5.2 Bioreduction6 Catalytic Asymmetric Conjugate Addition7 Conclusion

Synthesis of S-Licarbazepine by Asymmetric Reduction of Oxcarbazepine in Organic Solvent/Phosphate Buffer Biphasic System

2018 ◽  
Vol 921 ◽  
pp. 54-59
Author(s):  
Zhi Hin Ou ◽  
Jia Hui Xu
Keyword(s):  
Organic Solvent ◽  
Bacillus Anthracis ◽  
Efficient Method ◽  
Substrate Concentration ◽  
Phosphate Buffer ◽  
Dibutyl Phthalate ◽  
Cell Concentration ◽  
Asymmetric Reduction ◽  
Volume Ratio ◽  
Biphasic System

S-licarbazepine was synthesized by asymmetric reduction of oxcarbazepine in organic solvent/phosphate buffer biphasic system with Bacillus anthracis CGMCC No.12337 as catalyst. Effects of many factors on reduction were studied. Dibutyl phthalate/phosphate buffer was selected as the optimal biphasic system for reduction. The optimum reduction conditions are as follows: volume ratio of dibutyl phthalate and phosphate buffer 1:1, 30 g/L iospropanol as co-substrate, phosphate buffer pH 5, substrate concentration 7.92 mmol/L, cell concentration 30 g/L, 32°C，180 rpm. The conversion and enantiometric excess of S-licarbazepine reached 97.32% and 99.80%. An efficient method for synthesis of S-licarbazepine was provided.

A convenient synthesis of chiral succinic acid-d2 by catalytic asymmetric reduction using a ruthenium BINAP catalyst

1995 ◽  
Vol 6 (12) ◽  
pp. 2929-2932 ◽  
Author(s):  
Mohammad Shaharuzzaman ◽  
James Chickos ◽  
Cheok N. Tam ◽  
Timothy A. Keiderling
Keyword(s):  
Succinic Acid ◽  
Asymmetric Reduction ◽  
Convenient Synthesis ◽  
Catalytic Asymmetric

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.

Penicillamine as a ligand in the catalytic asymmetric reduction of ketones

2002 ◽  
Vol 80 (8) ◽  
pp. 885-888 ◽  
Author(s):  
Stephen Hanessian ◽  
Eric Jnoff ◽  
Andrew M Griffin
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Asymmetric Reduction ◽  
Catalytic Asymmetric ◽  
Reduction Of Ketones

Amino acids derived from D-penicillamine and thiazolidines were studied as ligands for the catalytic asymmetric reduction of ketones with borane. Enantioselectivities up to 83% ee were observed.Key words: asymmetric reduction, penicillamine, thiazolidine, amino acid.

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