Synthesis of beta -amino-alpha -hydroxy esters and beta -amino-alpha -azido ester by Sharpless asymmetric aminohydroxylation, byproducts analysis

Synthesis of enantiomerically pure beta -amino-alpha -hydroxy esters, e.g., I, and beta -amino-alpha -azido ester using Sharpless AA as a key step is described. A side reaction, the oxidn. of the beta -hydroxy-alpha -amino ester into the alpha ,alpha -di-tert-butyloxycarbamoyl-beta -ketoester under AA conditions, is also documented. [on SciFinder (R)]


Published in:
Journal of Organic Chemistry, 70, 7, 2847-2850
Year:
2005
Keywords:
Note:
CAN 142:410947
23-17
Aliphatic Compounds
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
0022-3263
written in English.
171738-31-1P; 482627-91-8P Role: BYP (Byproduct), PREP (Preparation) (byproducts from the stereoselective prepn. of amino hydroxy esters via Sharpless asym. aminohydroxylation of diisopropoxy(methoxy)cinnamate with t-Bu carbamate); 850404-78-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of (Boc-amino)azido[diisopropoxy(methoxy)phenyl]propanoate via mesylation of (Boc-amino)hydroxy[diisopropoxy(methoxy)phenyl]propanoate followed by azidation); 863301-53-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of (Boc-amino)hydroxy[diisopropoxy(methoxy)phenyl]propanoate via mesylation of (Boc-amino)hydroxy[diisopropoxy(methoxy)phenyl]propanoate followed by substitution); 850404-79-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of (Boc-amino)hydroxy[diisopropoxy(methoxy)phenyl]propanoate via mesylation of (Boc-amino)hydroxy[diisopropoxy(methoxy)phenyl]propanoate followed by substitution); 850404-75-0P Role: BYP (Byproduct), SPN (Synthetic preparation), PREP (Preparation) (prepn. of aryldi(Boc-amino)oxopropanoates via Sharpless aminohydroxylation of aryl(Boc-amino)hydroxypropanoates); 136620-75-2 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of aryldi(Boc-amino)oxopropanoates via Sharpless aminohydroxylation of aryl(Boc-amino)hydroxypropanoates); 850404-76-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of aryldi(Boc-amino)oxopropanoates via Sharpless aminohydroxylation of aryl(Boc-amino)hydroxypropanoates); 850404-77-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of(Boc-amino)azido[diisopropoxy(methoxy)phenyl]propanoate via mesylation of (Boc-amino)hydroxy[diisopropoxy(methoxy)phenyl]propanoate followed by azidation); 4248-19-5 (tert-Butyl carbamate); 850404-72-7 Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective prepn. of amino hydroxy esters via Sharpless asym. aminohydroxylation of diisopropoxy(methoxy)cinnamate with t-Bu carbamate); 850404-73-8P; 850404-74-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (stereoselective prepn. of amino hydroxy esters via Sharpless asym. aminohydroxylation of diisopropoxy(methoxy)cinnamate with t-Bu carbamate)
Laboratories:




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


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