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Tetrahedron

A versatile approach to pyrrolidine azasugars and homoazasugars based on a highly diastereoselective reductive benzyloxymethylation of protected tartarimide

X Zhou, WJ Liu, JL Ye, PQ Huang

文献索引:Zhou, Xiang; Liu, Wen-Jun; Ye, Jian-Liang; Huang, Pei-Qiang Tetrahedron, 2007 ,  vol. 63,  # 27  p. 6346 - 6357

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被引用次数: 48

摘要

A highly diastereoselective synthesis of enantio-enriched all trans-3, 4-dibenzyloxyl-5- benzyloxymethyl-2-pyrrolidinone 13a was developed based on SmI2-mediated benzyloxymethylation of O, O′-dibenzyltartarimide. The versatility of 13a and its antipode as the key building blocks for the asymmetric synthesis of pyrrolidine azasugars and homoazasugars has been demonstrated by elaborating them into naturally occurring DAB ...