The Strecker reaction coupled to Viedma ripening: a simple route to highly hindered enantiomerically pure amino acids

2018 ◽  
Vol 54 (77) ◽  
pp. 10832-10834 ◽  
Author(s):  
Iaroslav Baglai ◽  
Michel Leeman ◽  
Klaus Wurst ◽  
Bernard Kaptein ◽  
Richard M. Kellogg ◽  
...  
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Enantiomerically Pure ◽  
Simple Route ◽  
Strecker Reaction ◽  
Absolute Asymmetric Synthesis ◽  
Sterically Hindered ◽  
Proof Of Principle

We introduce a methodology based on a combination of the classical Strecker reaction, simple condensation and Viedma ripening, which allows absolute asymmetric synthesis of highly sterically hindered α-amino acids. As proof-of-principle, enantiomerically pure unnatural α-amino acids tert-leucine and α-(1-adamantyl)glycine have been obtained.

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

Absolute Asymmetric Synthesis of Tertiary α-Amino Acids

2012 ◽  
Vol 124 (20) ◽  
pp. 5065-5068 ◽  
Author(s):  
Thi Thoa Mai ◽  
Mathieu Branca ◽  
Didier Gori ◽  
Régis Guillot ◽  
Cyrille Kouklovsky ◽  
...  
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Absolute Asymmetric Synthesis

ChemInform Abstract: Absolute Asymmetric Synthesis of Tertiary α-Amino Acids.

ChemInform ◽  
2012 ◽  
Vol 43 (40) ◽  
pp. no-no
Author(s):  
Thi Thoa Mai ◽  
Mathieu Branca ◽  
Didier Gori ◽  
Regis Guillot ◽  
Cyrille Kouklovsky ◽  
...  
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Absolute Asymmetric Synthesis

Absolute Asymmetric Synthesis of Tertiary α-Amino Acids

2012 ◽  
Vol 51 (20) ◽  
pp. 4981-4984 ◽  
Author(s):  
Thi Thoa Mai ◽  
Mathieu Branca ◽  
Didier Gori ◽  
Régis Guillot ◽  
Cyrille Kouklovsky ◽  
...  
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Absolute Asymmetric Synthesis

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

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%).

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

Asymmetric synthesis of α-deuterated α-amino acids

2017 ◽  
Vol 15 (33) ◽  
pp. 6978-6983 ◽  
Author(s):  
Ryosuke Takeda ◽  
Hidenori Abe ◽  
Norio Shibata ◽  
Hiroki Moriwaki ◽  
Kunisuke Izawa ◽  
...  
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Pure Form ◽  
Enantiomerically Pure

A generalized approach for the preparation of α-2H-α-amino acids in enantiomerically pure form and with up to 99% deuteration is disclosed.

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