Efficient, Rhodium-Catalyzed Hydrogenation of α-Dehydroamino Acid Esters with Chiral Monodentate Aminophosphanes Bearing Two Binaphthyl Groups

2007 ◽  
Vol 2007 (32) ◽  
pp. 5395-5403 ◽  
Author(s):  
Luc Eberhardt ◽  
Dominique Armspach ◽  
Dominique Matt ◽  
Loic Toupet ◽  
Benoît Oswald
Keyword(s):  
Dehydroamino Acid ◽  
Acid Esters

Photochemistry of 2-azido-2-alkyl-3-oxobutanoic esters and amides

1990 ◽  
Vol 68 (8) ◽  
pp. 1425-1436 ◽  
Author(s):  
Oliver E. Edwards ◽  
Werner Rank
Keyword(s):  
Double Bond ◽  
Acyl Migration ◽  
Double Bond Migration ◽  
Keto Ester ◽  
Dehydroamino Acid ◽  
Acid Esters

Photolysis of 2-alkyl-2-azido-3-oxobutanoic esters and amides gave products resulting from alkyl or acyl migration onto nitrogen. The resulting ketimimes could be isolated in moderate purity, but the N-acyl imines were rapidly converted into solvation products or enamides (N-acetyl dehydroamino acid esters) resulting from double bond migration. Mechanisms for formation of these products are discussed. The N-(2-azido-2-methyl-3-oxobutanoyl) derivative of the diketopiperazine from L-valyl-L-proline gave a stereoisomer of the cyclol tripeptide unit of ergovaline. Keywords: N-acyl imines, mechanism of 2-azido-3-keto ester photolysis, cyclol tripeptide synthesis, ergovaline.

ChemInform Abstract: (Z)-Selective β-Bromination of N-Formyl-α,β- dehydroamino Acid Esters.

ChemInform ◽  
2010 ◽  
Vol 27 (31) ◽  
pp. no-no
Author(s):  
M. YAMADA ◽  
K. NAKAO ◽  
T. FUKUI ◽  
K. NUNAMI
Keyword(s):  
Dehydroamino Acid ◽  
Acid Esters
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