scholarly journals Enantioselective synthesis of α-alkenyl α-amino acids via N–H insertion reactions

2016 ◽  
Vol 7 (2) ◽  
pp. 1104-1108 ◽  
Author(s):  
Jun-Xia Guo ◽  
Ting Zhou ◽  
Bin Xu ◽  
Shou-Fei Zhu ◽  
Qi-Lin Zhou
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Enantioselective Synthesis ◽  
Insertion Reaction ◽  
Amino Acid Derivatives ◽  
Insertion Reactions ◽  
Phosphoric Acids

A new highly enantioselective route to α-alkenyl α-amino acid derivatives using a N–H insertion reaction of vinyldiazoacetates and tert-butyl carbamate cooperatively catalyzed by achiral dirhodium(ii) carboxylates and chiral spiro phosphoric acids was developed.

Enantioselective synthesis of β-amino acid derivatives via nickel-promoted regioselective carboxylation of ynamides and rhodium-catalyzed asymmetric hydrogenation

2016 ◽  
Vol 14 (42) ◽  
pp. 10080-10089 ◽  
Author(s):  
Nozomi Saito ◽  
Iman Abdullah ◽  
Kayoko Hayashi ◽  
Katsuyuki Hamada ◽  
Momoko Koyama ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Active Form ◽  
Asymmetric Hydrogenation ◽  
Optically Active ◽  
Enantioselective Synthesis ◽  
Amino Acid Derivatives

Nickel-promoted carboxylation of ynamides followed by rhodium-catalyzed asymmetric hydrogenation provided α-substituted-β-amino acids in an optically active form.

scholarly journals Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.02,6]decane skeleton

2009 ◽  
Vol 5 ◽  
Author(s):  
Matthias Breuning ◽  
Tobias Häuser ◽  
Christian Mehler ◽  
Christian Däschlein ◽  
Carsten Strohmann ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Building Blocks ◽  
Enantioselective Synthesis ◽  
Side Chain ◽  
Amino Acid Derivatives ◽  
Chiral Auxiliaries ◽  
Pyrrolidine Ring ◽  
Asymmetric Organocatalysis

An enantioselective route to four tricyclic amino acids and N-tosylamides, composed of a central norbornane framework with a 2-endo,3-endo-annelated pyrrolidine ring and a 5-endo-C1 or -C2 side chain, has been developed. A key intermediate was the chiral, N-Boc-protected ketone (1R,2S,6S,7R)-4-azatricyclo[5.2.1.02,6]decan-8-one, available from inexpensive endo-carbic anhydride in five steps and 47% yield. The rigid scaffold makes these amino acid derivatives promising candidates for β-turn-inducing building blocks in peptidomimetics and for chiral auxiliaries in asymmetric organocatalysis.

Enantioselective synthesis of cyclic quaternary α-amino acid derivatives by chiral phosphoric acid catalysis

2017 ◽  
Vol 15 (28) ◽  
pp. 6033-6041 ◽  
Author(s):  
Lei Wang ◽  
Abdul Rahman ◽  
Xufeng Lin
Keyword(s):  
Amino Acid ◽  
Phosphoric Acid ◽  
Acid Catalysis ◽  
Enantioselective Synthesis ◽  
Amino Acid Derivatives ◽  
Chiral Phosphoric Acid ◽  
Efficient Route ◽  
Quaternary Stereocenter ◽  
High Yields ◽  
Phosphoric Acids

Development of highly enantioselective aza-Friedel–Crafts reaction of N-sulfonyl cyclic ketimines with indoles catalyzed by chiral phosphoric acids, providing an efficient route to indole-containing chiral cyclic α-amino acid derivatives bearing quaternary stereocenter in high yields and up to 98% enantioselectivity.

An enantioselective synthesis of β2-amino acid derivatives

2005 ◽  
Vol 16 (7) ◽  
pp. 1309-1319 ◽  
Author(s):  
Jomana Elaridi ◽  
Ali Thaqi ◽  
Andrew Prosser ◽  
W. Roy Jackson ◽  
Andrea J. Robinson
Keyword(s):  
Amino Acid ◽  
Enantioselective Synthesis ◽  
Amino Acid Derivatives

Synthesis of New β-Amino Acids via 5-Oxazolidinones and the Arndt - Eistert Procedure

2005 ◽  
Vol 58 (11) ◽  
pp. 778 ◽  
Author(s):  
Andrew B. Hughes ◽  
Brad E. Sleebs
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Reductive Cleavage ◽  
High Yield ◽  
Amino Acid Derivatives ◽  
Peptide Therapeutics

N-Methyl β-amino acids are potentially useful amino acid derivatives for incorporation in lead peptide therapeutics. The syntheses of five such compounds are presented. Their synthesis via 6-oxazinanones was low yielding. Alternatively, reductive cleavage of a 5-oxazolidinone gave the N-methyl α-amino acid, which was then homologated via an Arndt–Eistert procedure in high yield to give the N-methyl β-amino acid.

Chiral sensors for determining the absolute configurations of α-amino acid derivatives

2018 ◽  
Vol 16 (37) ◽  
pp. 8311-8317 ◽  
Author(s):  
Zhongxiang Chen ◽  
Hongjun Fan ◽  
Shiwei Yang ◽  
Guangling Bian ◽  
Ling Song
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Amino Acid Derivatives ◽  
H Nmr ◽  
The Absolute

Two simple 1H NMR tests give the absolute configurations of α-amino acids.

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