73148-44-4Relevant academic research and scientific papers
Enantioselective Michael reactions of chiral secondary enaminoesters with 2-substituted nitroethylenes. Syntheses of trans,trans-2,4-disubstituted pyrrolidine-3-carboxylates
Revial, Gilbert,Lim, Sethy,Viossat, Bernard,Lemoine, Pascale,Tomas, Alain,Duprat, Arthur F.,Pfau, Michel
, p. 4593 - 4600 (2007/10/03)
The Michael reaction of chiral 3-substituted secondary enaminoesters with 2-substituted nitroethylenes leads to (Z)-adducts, with good to excellent diastereoselectivity. The nitro group of these adducts was catalytically reduced to give, after cyclization and chiral amine elimination, pyrrolines or pyrrolidines after further reduction. In particular, the syntheses of ethyl (2R,3S,4S)-2,4-dimethylpyrrolidine-3-carboxylate and ethyl (2R,3R,4S)-2-(4-methoxyphenyl)-4-(3,4-(methylenedioxy)phenyl)pyrrolidine-3-ca rboxylate are described.
A versatile route to β-enamino esters by acylation of lithium enamines with diethyl carbonate or benzyl chloroformate
Bartoli, Giuseppe,Cimarelli, Cristina,Dalpozzo, Renato,Palmieri, Gianni
, p. 8613 - 8622 (2007/10/02)
A versatile route to β-enamino esters 1, using accessible starting materials, was developed. Lithiated enamines are allowed to react with diethyl carbonate or benzyl chloroformate with the formation of the β-enamino esters 1a or 1b. The reaction is rather general from a wide array of ketimines and aldimines. Products included cyclic β-enamino esters 1aa-ac, very useful for the synthesis of natural products.
