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

Lepine, RenaudCarbonnelle, Anny-ClaudeZhu, Jieping2010-11-252010-11-252010-11-25200310.1055/s-2003-40840https://infoscience.epfl.ch/handle/20.500.14299/58489Synthesis of orthogonally protected (2S,4R)- and (2S,4S)-4-hydroxyornithines I is reported featuring an asym. alkylation of N-(diphenylmethylene)glycine tert-Bu ester with (5S)-N-benzyloxycarbonyl-5-iodomethyl oxazolidine. Double stereoselection was examd. using chiral ammonium salts as phase transfer catalysts, and a substrate-directed chiral induction is documented. [on SciFinder (R)]Asymmetric synthesis and induction (asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); Amino acids Role: SPN (Synthetic preparation)PREP (Preparation) (esters; asym. synthesis of orthogonally protected hydroxyornithines and their derivs.)ornithine hydroxy orthogonally protected asym synthesisAsymmetric synthesis of orthogonally protected (2S,4R)- and (2S,4S)-4-hydroxyornithinetext::journal::journal article::research article