The first enantioselective synthesis of the amino acid, (2S,3S,4R)-γ-hydroxyisoleucine using a palladium(ii) catalysed 3,3-sigmatropic rearrangement

2004 ◽  
Vol 2 (6) ◽  
pp. 808-809 ◽  
Author(s):  
Andrew G. Jamieson ◽  
Andrew Sutherland ◽  
Christine L. Willis
Keyword(s):  
Amino Acid ◽  
Sigmatropic Rearrangement ◽  
Enantioselective Synthesis

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

Enantioselective Synthesis and Photoreactivity of a Diazirinyl-substituted (R)-β-Phenylalanine

2014 ◽  
Vol 69 (11-12) ◽  
pp. 1088-1096 ◽  
Author(s):  
Jan-Niklas Schäckermann ◽  
Thomas Lindel
Keyword(s):  
Amino Acid ◽  
Absolute Configuration ◽  
Enantioselective Synthesis ◽  
Thermally Stable ◽  
Standard Laboratory ◽  
Laboratory Conditions ◽  
Quantumchemical Calculations ◽  
Valence Tautomers ◽  
The Absolute

Abstract The first enantioselective synthesis of a photoreactive (R)-β-phenylalanine is described. In the key step, m-diazirinyl-substituted benzaldehyde is converted to a chiral sulfinimine in a Ti(OEt)4- mediated reaction, followed by diastereoselective enolate addition. The absolute configuration of photo (R)-β-phenylalanine was confirmed by Mosher analysis. The photo amino acid proved to be thermally stable under standard laboratory conditions. Irradiation in toluene afforded cycloheptatriene=norcaradiene valence tautomers, together with carbene benzylation. Quantumchemical calculations indicate a small triplet-singlet gap.

Dearomative [2,3] sigmatropic rearrangement of ammonium ylides followed by 1,4-elimination to form α-(ortho-vinylphenyl)amino acid esters

2018 ◽  
Vol 16 (26) ◽  
pp. 4833-4839 ◽  
Author(s):  
Eiji Tayama ◽  
Sho Sotome
Keyword(s):  
Amino Acid ◽  
Sigmatropic Rearrangement ◽  
Amino Acid Esters ◽  
Acid Esters

A base-induced dearomative [2,3] sigmatropic rearrangement followed by 1,4-elimination produced α-(ortho-vinylphenyl)amino acid esters.

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.

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