scholarly journals Stereodivergent entry to β-branched β-trifluoromethyl α-amino acid derivatives by sequential catalytic asymmetric reactions

2021 ◽  
Author(s):  
Vasco Corti ◽  
Riccardo Riccioli ◽  
Ada Martinelli ◽  
Sofia Sandri ◽  
Mariafrancesca Fochi ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Asymmetric Reactions ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Catalytic Asymmetric ◽  
Catalytic Asymmetric Reactions

Currently, conventional reductive catalytic methodologies do not guarantee general access to enantioenriched β-branched β-trifluoromethyl α-amino acid derivatives. Herein, a one-pot approach to these important α-amino acids, grounded on the reduction...

One-pot synthesis of β-amino acid derivatives from α-amino acids

2006 ◽  
Vol 47 (49) ◽  
pp. 8757-8760 ◽  
Author(s):  
Carlos J. Saavedra ◽  
Rosendo Hernández ◽  
Alicia Boto ◽  
Eleuterio Álvarez
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
One Pot Synthesis

One-Pot Synthesis of β-Amino Acid Derivatives from α-Amino Acids.

ChemInform ◽  
2007 ◽  
Vol 38 (13) ◽  
Author(s):  
Carlos J. Saavedra ◽  
Rosendo Hernandez ◽  
Alicia Boto ◽  
Eleuterio Alvarez
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
One Pot Synthesis

scholarly journals Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction

2011 ◽  
Vol 7 ◽  
pp. 1570-1576 ◽  
Author(s):  
Elizabeth P Jones ◽  
Peter Jones ◽  
Andrew J P White ◽  
Anthony G M Barrett
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Nucleophilic Addition ◽  
Ring Opening ◽  
Coupling Reaction ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Aryl Group ◽  
Hydrolysis Of

A method was developed for the synthesis of α-alkyl, α-aryl-bislactim ethers in good to excellent yields and high diastereoselectivities, consisting of a facile one-pot procedure in which the aryl group is introduced by means of a nucleophilic addition to benzyne and the alkyl group by alkylation of a resultant benzylic anion. Hydrolysis of the sterically less hindered adducts gave the corresponding quaternary amino acids with no racemization, whereas hydrolytic ring opening gave the corresponding valine dipeptides from bulkier bislactims.

Stereoselective syntheses of α-amino acid and peptide derivatives by the U-4CR of 5-desoxy-5-thio-D-xylopyranosylamine

2001 ◽  
Vol 79 (12) ◽  
pp. 1934-1939 ◽  
Author(s):  
Günther Ross ◽  
Ivar Ugi
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Chiral Amine ◽  
Peptide Derivatives ◽  
Stereoselective Syntheses

Since 1961, the synthesis of α-amino acids derivatives by the four-component reaction of isocyanides (U-4CR) as a one-pot reaction has been developed. Only recently it was found that a variety of these α-amino acids compounds can be formed stereoselectively by the U-4CR using 1-amino-5-deoxy-5-thio-2,3,4-tri-O-isobutanoyl-β-D-xylopyranose as the amine component. The stereoselectivity inducing auxiliary 5-desoxy-5-thio-D-xylopyranosyl group of the so-formed products can be replaced selectively by hydrogen.Key words: stereoselective U-4CR, chiral amine component, amino carbohydrate, α-amino acid derivatives.

scholarly journals Catalytic asymmetric propargyl- and allylboration of hydrazonoesters: a metal-free approach to sterically encumbered chiral α-amino acid derivatives

2018 ◽  
Vol 54 (91) ◽  
pp. 12852-12855 ◽  
Author(s):  
Sybrand J. T. Jonker ◽  
Colin Diner ◽  
Göran Schulz ◽  
Hiroaki Iwamoto ◽  
Lars Eriksson ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Asymmetric Catalysis ◽  
Amino Acid Derivatives ◽  
Metal Free ◽  
Catalytic Asymmetric

Metal-free asymmetric catalysis for the synthesis of sterically encumbered amino-acids was developed using allyl- and allenylboronic acid reagents.

scholarly journals Catalytic asymmetric synthesis of quaternary trifluoromethyl α- to ε-amino acid derivatives via umpolung allylation/2-aza-Cope rearrangement

2020 ◽  
Vol 11 (40) ◽  
pp. 10984-10990 ◽  
Author(s):  
Xi-Shang Sun ◽  
Xing-Heng Wang ◽  
Hai-Yan Tao ◽  
Liang Wei ◽  
Chun-Jiang Wang
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Amino Acid Derivatives ◽  
Cope Rearrangement ◽  
Catalytic Asymmetric Synthesis ◽  
Catalytic Asymmetric ◽  
High Yields

In this study, we developed an efficient Ir-catalyzed cascade umpolung allylation/2-aza-Cope rearrangement for the preparation of a variety of quaternary trifluoromethyl α-ε-amino acids in high yields with excellent enantioselectivities.

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