Radical addition of nitrones to acrylates mediated by SmI2: asymmetric synthesis of γ-amino acids employing carbohydrate-based chiral auxiliaries

2004 ◽  
pp. 1962-1963 ◽  
Author(s):  
Sine A. Johannesen ◽  
Silvia Albu ◽  
Rita G. Hazell ◽  
Troels Skrydstrup
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Radical Addition ◽  
Chiral Auxiliaries

Novel Intermolecular Carbon Radical Addition to a Nitrone: Asymmetric Synthesis of α-Amino Acids.

ChemInform ◽  
2003 ◽  
Vol 34 (23) ◽  
Author(s):  
Masafumi Ueda ◽  
Hideto Miyabe ◽  
Masako Teramachi ◽  
Okiko Miyata ◽  
Takeaki Naito
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Radical Addition

Asymmetric Synthesis of α-Amino Acids Based on Carbon Radical Addition to Glyoxylic Oxime Ether

2000 ◽  
Vol 65 (1) ◽  
pp. 176-185 ◽  
Author(s):  
Hideto Miyabe ◽  
Chikage Ushiro ◽  
Masafumi Ueda ◽  
Kumiko Yamakawa ◽  
Takeaki Naito
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Radical Addition ◽  
Oxime Ether

Rapid asymmetric synthesis of amino acids via NiII complexes based on new fluorine containing chiral auxiliaries

2010 ◽  
Vol 21 (24) ◽  
pp. 2956-2965 ◽  
Author(s):  
Ashot S. Saghyan ◽  
Ani S. Dadayan ◽  
Slavik A. Dadayan ◽  
Anna F. Mkrtchyan ◽  
Arpine V. Geolchanyan ◽  
...  
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Chiral Auxiliaries

Asymmetric Synthesis of Enantiomerically Enriched a-Amino Acids Containing 2-Furyl- and 2-Thienyl-1,2,4-triazoles in the Side-Chain

2014 ◽  
Vol 69 (4) ◽  
pp. 451-460 ◽  
Author(s):  
Ashot S. Saghyan ◽  
Hayarpi M. Simonyan ◽  
Satenik G. Petrosyan ◽  
Anna F. Mkrtchyan ◽  
Lilit V. Khachatryan ◽  
...  
Keyword(s):  
Amino Acids ◽  
Schiff Base ◽  
Asymmetric Synthesis ◽  
Efficient Method ◽  
Enantiomeric Excess ◽  
Side Chain ◽  
Chiral Auxiliaries ◽  
Enantiomerically Pure ◽  
Dehydroamino Acids ◽  
Hydrolysis Of

An efficient method for the asymmetric synthesis of a-amino acids, containing furyl- and thiophenyl-substituted triazoles in their side-chain, is reported. The strategy relies on Michael addition of 3,4,5-substituted 1,2,4-triazoles to the C=C bond of chiral NiII complexes containing the Schiff base formed from dehydroamino acids (dehydroalanine and (E + Z)-dehydroaminobutyric acid) and from chiral auxiliaries, i. e. (S)-2-N-(N0-benzylprolyl)aminobenzophenone and (S)-2-N- (N0-2-chlorobenzylprolyl) aminobenzophenone. The reactions proceeded with good to very good diastereoselectivity. Hydrolysis of the diastereomeric mixtures of metal complexes afforded the enantiomerically pure a-amino acids with high enantiomeric excess (ee> 98%).

Sign in / Sign up

Export Citation Format

Share Document