Chiral Auxiliaries with a Switching Center:  New Tools in Asymmetric Synthesis. Application to the Synthesis of Enantiomerically Pure (R)- and (S)-α-Amino Acids

1998 ◽  
Vol 63 (23) ◽  
pp. 8094-8095 ◽  
Author(s):  
Luc Meyer ◽  
Jean-Marie Poirier ◽  
Pierre Duhamel ◽  
Lucette Duhamel
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Chiral Auxiliaries ◽  
Enantiomerically Pure

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%).

ChemInform Abstract: Chiral Auxiliaries with a Switching Center: New Tools in Asymmetric Synthesis. Application to the Synthesis of Enantiomerically Pure (R)- and (S)-α-Amino Acids.

ChemInform ◽  
2010 ◽  
Vol 30 (15) ◽  
pp. no-no
Author(s):  
Luc Meyer ◽  
Jean-Marie Poirier ◽  
Pierre Duhamel ◽  
Lucette Duhamel
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Chiral Auxiliaries ◽  
Enantiomerically Pure

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

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

ChemInform Abstract: Preparation of Enantiomerically Pure Perfluorobutanesulfinamide and Its Application to the Asymmetric Synthesis of α-Amino Acids.

ChemInform ◽  
2016 ◽  
Vol 47 (28) ◽  
Author(s):  
Apiwat Wangweerawong ◽  
Joshua R. Hummel ◽  
Robert G. Bergman ◽  
Jonathan A. Ellman
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Enantiomerically Pure

scholarly journals Preparation of Enantiomerically Pure Perfluorobutanesulfinamide and Its Application to the Asymmetric Synthesis of α-Amino Acids

2016 ◽  
Vol 81 (4) ◽  
pp. 1547-1557 ◽  
Author(s):  
Apiwat Wangweerawong ◽  
Joshua R. Hummel ◽  
Robert G. Bergman ◽  
Jonathan A. Ellman
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Enantiomerically Pure

ChemInform Abstract: Asymmetric Synthesis Employing a Chiral 5-Methoxy-1,4-oxazin-2-one Derivative: Preparation of Enantiomerically Pure α-Quaternary α-Amino Acids.

ChemInform ◽  
2010 ◽  
Vol 30 (47) ◽  
pp. no-no
Author(s):  
Oliver Achatz ◽  
Andrea Grandl ◽  
Klaus Theodor Wanner
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Enantiomerically Pure

ChemInform Abstract: Stereoselective α-Alkylation of New Chiral Auxiliaries: An Access to Enantiomerically Pure α- and α,β-Substituted β-Amino Acids.

ChemInform ◽  
2010 ◽  
Vol 31 (5) ◽  
pp. no-no
Author(s):  
Claude Agami ◽  
Sandrine Cheramy ◽  
Luc Dechoux
Keyword(s):  
Amino Acids ◽  
Chiral Auxiliaries ◽  
Enantiomerically Pure

Halo-substituted (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamides as New Chiral Auxiliaries for the Asymmetric Synthesis of (S)-α-Amino Acids.

ChemInform ◽  
2003 ◽  
Vol 34 (12) ◽  
Author(s):  
Yu. N. Belokon ◽  
V. I. Maleev ◽  
A. A. Petrosyan ◽  
T. F. Savel'eva ◽  
N. S. Ikonnikov ◽  
...  
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Chiral Auxiliaries

Stereoselective α-Alkylation of New Chiral Auxiliaries: An Access to Enantiomerically Pure α- and α,β-Substituted β-Amino Acids

Synlett ◽  
1999 ◽  
Vol 1999 (11) ◽  
pp. 1838-1840 ◽  
Author(s):  
Claude Agami ◽  
Sandrine Cheramy ◽  
Luc Dechoux
Keyword(s):  
Amino Acids ◽  
Chiral Auxiliaries ◽  
Enantiomerically Pure
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