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

Synthesis 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)]


Published in:
Synlett, 10, 1455-1458
Year:
2003
Keywords:
Note:
CAN 140:16939
34-2
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles, CNRS,Gif-sur-Yvette,Fr.
Journal
0936-5214
written in English.
61278-21-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (N-protection; asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 1643-19-2 (Tetrabutylammonium bromide); 200132-54-3; 219601-70-4; 534570-50-8 Role: CAT (Catalyst use), USES (Uses) (asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 630400-90-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 329912-53-0P; 371972-14-4P; 630400-89-4P Role: SPN (Synthetic preparation), PREP (Preparation) (asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 23788-74-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (azidation; asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 81477-94-3 Role: RCT (Reactant), RACT (Reactant or reagent) (coupling with (iodomethyl)oxazolidine; asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 630400-88-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (coupling with imino ester; asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 630400-87-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (iodination; asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 135582-93-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (monotosylation; asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 630400-86-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (oxazolidine ring closure; asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 85820-82-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (redn./ring opening; asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 13139-17-8; 22323-82-6 Role: RCT (Reactant), RACT (Reactant or reagent) (tosylation; asym. synthesis of orthogonally protected hydroxyornithines and their derivs.)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


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