A Convenient Synthesis and the Asymmetric Hydrogenation ofN-Phthaloyl Dehydroamino Acid Esters

2008 ◽  
Vol 10 (14) ◽  
pp. 3033-3036 ◽  
Author(s):  
Jian Chen ◽  
Qiang Liu ◽  
Weicheng Zhang ◽  
Stephen Spinella ◽  
Aiwen Lei ◽  
...  
Keyword(s):  
Asymmetric Hydrogenation ◽  
Convenient Synthesis ◽  
Dehydroamino Acid ◽  
Acid Esters

ChemInform Abstract: A Convenient Synthesis and the Asymmetric Hydrogenation of N-Phthaloyl Dehydroamino Acid Esters.

ChemInform ◽  
2008 ◽  
Vol 39 (47) ◽  
Author(s):  
Jian Chen ◽  
Qiang Liu ◽  
Weicheng Zhang ◽  
Stephen Spinella ◽  
Aiwen Lei ◽  
...  
Keyword(s):  
Asymmetric Hydrogenation ◽  
Convenient Synthesis ◽  
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.

scholarly journals Alkoxide-induced ring opening of bicyclic 2-vinylcyclobutanones: A convenient synthesis of 2-vinyl-substituted 3-cycloalkene-1-carboxylic acid esters

2012 ◽  
Vol 8 ◽  
pp. 650-657 ◽  
Author(s):  
Xiufang Ji ◽  
Zhiming Li ◽  
Quanrui Wang ◽  
Andreas Goeke
Keyword(s):  
Carboxylic Acid ◽  
Ring Opening ◽  
Claisen Rearrangement ◽  
Ring Cleavage ◽  
Unsaturated Ester ◽  
Supplementary Method ◽  
Convenient Synthesis ◽  
High Yields ◽  
Acid Esters

The fused 2-vinyl or 2-phenyl substituted cyclobutanones 4 undergo stereoselective ring openings by the action of alkoxide ions (t-BuO− or MeO−) to produce novel vicinally disubstituted cycloalkene derivatives 5 and 6 in moderate to high yields. The ring cleavage usually occurs with complete regioselectivity. The accessibility of γ,δ-unsaturated ester or acid derivatives makes this transformation a good supplementary method for the well-established Johnson–Claisen rearrangement.

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
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