Optically Active Aromatic and Heteroaromatic α-Amino Acids by a One-Pot Catalytic Enantioselective Addition of Aromatic and Heteroaromatic C−H Bonds to α-Imino Esters

2002 ◽  
Vol 67 (12) ◽  
pp. 4352-4361 ◽  
Author(s):  
Steen Saaby ◽  
Pau Bayón ◽  
Pompiliu S. Aburel ◽  
Karl Anker Jørgensen
Keyword(s):  
Amino Acids ◽  
Optically Active ◽  
One Pot ◽  
Enantioselective Addition ◽  
Imino Esters

Catalytic Approach for the Formation of Optically Active Allyl α-Amino Acids by Addition of Allylic Metal Compounds to α-Imino Esters

1999 ◽  
Vol 64 (13) ◽  
pp. 4844-4849 ◽  
Author(s):  
Xiangming Fang ◽  
Mogens Johannsen ◽  
Sulan Yao ◽  
Nicholas Gathergood ◽  
Rita G. Hazell ◽  
...  
Keyword(s):  
Amino Acids ◽  
Optically Active ◽  
Metal Compounds ◽  
Imino Esters

First One-Pot Copper-Catalyzed Synthesis of α-Hydroxy-β-amino Acids in Water. A New Protocol for Preparation of Optically Active Norstatines (VI).

ChemInform ◽  
2004 ◽  
Vol 35 (3) ◽  
Author(s):  
Francesco Fringuelli ◽  
Ferdinando Pizzo ◽  
Mauro Rucci ◽  
Luigi Vaccaro
Keyword(s):  
Amino Acids ◽  
Optically Active ◽  
One Pot

Isoxazolinium Salts in Asymmetric Synthesis. 1. Stereoselective Reduction Induced by a 3’-Alkoxy Stereocentre. A New Approach to Polyfunctionalized β-Amino Acids* [1, 2]

2004 ◽  
Vol 59 (4) ◽  
pp. 451-467 ◽  
Author(s):  
Marco Henneböhle ◽  
Pierre-Yves Le Roy ◽  
Matthias Hein ◽  
Rudolf Ehrler ◽  
Volker Jäger
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Catalytic Hydrogenation ◽  
Optically Active ◽  
Side Chain ◽  
Reduction Step ◽  
One Pot ◽  
New Approach ◽  
Stereoselective Reduction

AbstractA new approach to optically active N-methylamino acids is presented, relying on stereoselective reduction of N-methylisoxazolinium salts with a dioxyethyl side-chain. The diastereoselectivity of the reduction step is studied systematically, in comparison with that of respective isoxazolines. A two-step transformation of isoxazolinium salts - with NaBH3(OAc) and subsequent catalytic hydrogenation as well as a one-pot reduction by catalytic hydrogenation led to high (95:5 and 87:13) diastereomeric ratios of protected erythro-N-methylaminopentanetriols. The hydroxyethyl side-chain is elaborated by oxidation to afford the β -N-methylamino acid 37, exemplifying the potential of this strategy.

ChemInform Abstract: Formation of Optically Active Aromatic α-Amino Acids by Catalytic Enantioselective Addition of Imines to Aromatic Compounds.

ChemInform ◽  
2001 ◽  
Vol 32 (13) ◽  
pp. no-no
Author(s):  
Steen Saaby ◽  
Xiangming Fang ◽  
Nicholas Gathergood ◽  
Karl Anker Joergensen
Keyword(s):  
Amino Acids ◽  
Aromatic Compounds ◽  
Optically Active ◽  
Enantioselective Addition

One-pot Synthesis of Optically Active Tetramic Acids from Amino Acids Mediated by 1-Hydroxybenzotriazole

Synlett ◽  
2001 ◽  
Vol 2001 (10) ◽  
pp. 1653-1655 ◽  
Author(s):  
Giorgos Athanasellis ◽  
Efstathios Gavrielatos ◽  
Olga Igglessi-Markopoulou
Keyword(s):  
Amino Acids ◽  
Optically Active ◽  
One Pot ◽  
One Pot Synthesis ◽  
Tetramic Acids

First One-Pot Copper-Catalyzed Synthesis of α-Hydroxy-β-Amino Acids in Water. A New Protocol for Preparation of Optically Active Norstatines

2003 ◽  
Vol 68 (18) ◽  
pp. 7041-7045 ◽  
Author(s):  
Francesco Fringuelli ◽  
Ferdinando Pizzo ◽  
Mauro Rucci ◽  
Luigi Vaccaro
Keyword(s):  
Amino Acids ◽  
Optically Active ◽  
One Pot
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