Synlett

Asymmetric synthesis of orthogonally protected (2S, 4R)-and (2S, 4S)-4-hydroxyornithine

R Lepine, AC Carbonnelle, J Zhu

文献索引：Lepine, Renaud; Carbonnelle, Anny-Claude; Zhu, Jieping Synlett, 2003 , # 10 p. 1455 - 1458

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被引用次数: 11

摘要

Abstract Synthesis of orthogonally protected (2S, 4R)-and (2S, 4S)-4-hydroxyornithine was reported featuring an asymmetric alkylation of N-(diphenylmethylene) glycine tert-butyl ester (6) by (5S)-N-benzyloxycarbonyl-5-iodomethyl oxazolidine (7). Double stereoselection was examined using chiral ammonium salts as phase transfer catalysts and a substrate-directed chiral induction is documented.