Enantioselective Michael reactions of chiral secondary enaminoesters with 2-substituted nitroethylenes. Syntheses of trans, trans-2, 4-disubstituted pyrrolidine-3- …

…, P Lemoine, A Tomas, AF Duprat, M Pfau

文献索引：Revial, Gilbert; Lim, Sethy; Viossat, Bernard; Lemoine, Pascale; Tomas, Alain; Duprat, Arthur F.; Pfau, Michel Journal of Organic Chemistry, 2000 , vol. 65, # 15 p. 4593 - 4600

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被引用次数: 31

摘要

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 (2 R, 3 S, 4 S)-2, 4-dimethylpyrrolidine-3-carboxylate and ethyl (2 R, 3 R, 4 S)-2-(4- ...