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Handy access to chiral N, N′-disubstituted 3-aminopyrrolidines.

J Maddaluno, A Corruble, V Leroux, G Plé…

文献索引:Maddaluno; Corruble; Leroux; Ple; Duhamel Tetrahedron Asymmetry, 1992 , vol. 3, # 10 p. 1239 - 1242

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被引用次数: 22

摘要

Abstract: A new and rapid synthesis of (S)-3-aminopyrrolidines z is proposed from N- protected (S)-Asparagine. Basic cyclization of methyl NZ-(S)-Asparaginate 1 followed by onepot N-benzylation directly leads to (S)-aminosuccinimide 3 which, after cleavage of the Z- protecting group, is converted to corresponding imines and readily reduced to disubstitut~ chiral 3-aminopy~ olidines 2. Almost no ra~ emization (~ 5%) of the original amino-acid as ...