Asymmetric synthesis of heteroorganic analogs of natural compounds. 2. A convenient preparative method for the synthesis of enantiomerically pure (S)-(-)-o-, m-, and p-fluorophenylalanines and their 2-methylsubstituted analogs

1990 ◽  
Vol 39 (7) ◽  
pp. 1479-1485 ◽  
Author(s):  
V. A. Soloshonok ◽  
Yu. N. Belokon' ◽  
V. P. Kukhar' ◽  
N. I. Chernoglazova ◽  
M. B. Saporovskaya ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Natural Compounds ◽  
Preparative Method ◽  
Enantiomerically Pure

scholarly journals Preparative Method for Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid

Molecules ◽  
2019 ◽  
Vol 24 (24) ◽  
pp. 4521 ◽  
Author(s):  
Jianlin Han ◽  
Ryosuke Takeda ◽  
Xinyi Liu ◽  
Hiroyuki Konno ◽  
Hidenori Abe ◽  
...  
Keyword(s):  
Schiff Base ◽  
Drug Design ◽  
Asymmetric Synthesis ◽  
Large Scale ◽  
Preparative Method ◽  
Chiral Auxiliary ◽  
Enantiomerically Pure ◽  
Great Demand ◽  
Derivatives Of

Enantiomerically pure derivatives of 2-amino-4,4,4-trifluorobutanoic acid are in great demand as bioisostere of leucine moiety in the drug design. Here, we disclose a method specifically developed for large-scale (>150 g) preparation of the target (S)-N-Fmoc-2-amino-4,4,4-trifluorobutanoic acid. The method employs a recyclable chiral auxiliary to form the corresponding Ni(II) complex with glycine Schiff base, which is alkylated with CF3–CH2–I under basic conditions. The resultant alkylated Ni(II) complex is disassembled to reclaim the chiral auxiliary and 2-amino-4,4,4-trifluorobutanoic acid, which is in situ converted to the N-Fmoc derivative. The whole procedure was reproduced several times for consecutive preparation of over 300 g of the target (S)-N-Fmoc-2-amino-4,4,4-trifluorobutanoic acid.

Indium Bromide-catalyzed Unprecedented Hydrogenolysis: A Novel One-Pot Synthesis of Per-O-Acetylated β-carboxymethyl O and S-glycosides

2020 ◽  
Vol 24 (8) ◽  
pp. 900-908
Author(s):  
Ram Naresh Yadav ◽  
Amrendra K Singh ◽  
Bimal Banik
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Auxiliary ◽  
Bioactive Molecules ◽  
One Pot ◽  
Enantiomerically Pure ◽  
Stereoselective Glycosylation ◽  
One Pot Synthesis ◽  
Wide Range

Numerous O (oxa)- and S (thia)-glycosyl esters and their analogous glycosyl acids have been accomplished through stereoselective glycosylation of various peracetylated bromo sugar with benzyl glycolate using InBr3 as a glycosyl promotor followed by in situ hydrogenolysis of resulting glycosyl ester. A tandem glycosylating and hydrogenolytic activity of InBr3 has been successfully investigated in a one-pot procedure. The resulting synthetically valuable and virtually unexplored class of β-CMGL (glycosyl acids) could serve as an excellent potential chiral auxiliary in the asymmetric synthesis of a wide range of enantiomerically pure medicinally prevalent β-lactams and other bioactive molecules of diverse medicinal interest.

Asymmetric synthesis of enantiomerically pure 7-isopropenyl-4a-methyl-3-methyleneoctahydrochromen-2-ones

2007 ◽  
Vol 18 (22) ◽  
pp. 2712-2718 ◽  
Author(s):  
Henryk Krawczyk ◽  
Marcin Śliwiński ◽  
Jacek Kędzia ◽  
Jakub Wojciechowski ◽  
Wojciech M. Wolf
Keyword(s):  
Asymmetric Synthesis ◽  
Enantiomerically Pure
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