Truncated diastereoselective Passerini reaction, a rapid construction of polysubstituted oxazole and peptides having an alpha -hydroxy-beta -amino acid component
The reaction of aldehydes and ketones, including aliph. and arom. ones, with amides of alpha -isocyano-beta -phenylpropionic acid in toluene in the presence of lithium bromide gives 2,4,5-trisubstituted oxazoles in good to excellent yield. Protected chiral alpha -amino aldehydes participate in this reaction to give, after hydrolysis of the oxazoles, norstatine-contg. peptides in good overall yield. The nucleophilic addn. of isonitriles to N,N-dibenzylphenylalanal is investigated for the first time and is found to be stereoselective leading predominantly to the anti-adduct (dr = 9/1). On the other hand, the reaction between the N-Boc phenylalanal and isonitrile is non-stereoselective. [on SciFinder (R)]
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Cuny, G., Gamez-Montano, R., & Zhu, J. (2004). Truncated diastereoselective Passerini reaction, a rapid construction of polysubstituted oxazole and peptides having an alpha -hydroxy-beta -amino acid component. Tetrahedron, 60(22), 4879–4885. https://doi.org/10.1016/j.tet.2004.03.084
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2004
60
22
4879
4885
CAN 141:157450
34-3
Amino Acids, Peptides, and Proteins
CNRS, Institut de Chimie des Substances Naturelles,Gif-sur-Yvette,Fr.
Journal
written in English.
78-84-2 (Isobutyraldehyde); 111-71-7 (Heptanal); 529-20-4 (o Tolualdehyde); 555-16-8; 609-09-6 (Diethyl oxomalonate); 924-44-7 (Ethyl oxoacetate); 3132-99-8 (3 Bromobenzaldehyde); 72155-45-4; 85059-38-7; 111060-64-1; 120301-87-3; 500555-97-5; 619335-56-7 Role: RCT (Reactant), RACT (Reactant or reagent) (synthesis of oxazoles and peptides having alpha -hydroxy-beta -amino acid component by diastereoselective Passerini reaction); 85059-48-9P; 619335-57-8P; 728041-37-0P; 728041-39-2P; 728041-40-5P; 728041-41-6P; 728041-42-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (synthesis of oxazoles and peptides having alpha -hydroxy-beta -amino acid component by diastereoselective Passerini reaction); 728041-22-3P; 728041-23-4P; 728041-24-5P; 728041-25-6P; 728041-26-7P; 728041-27-8P; 728041-28-9P; 728041-29-0P; 728041-30-3P; 728041-31-4P; 728041-32-5P; 728041-33-6P; 728041-34-7P; 728041-35-8P; 728041-36-9P; 728041-38-1P; 728041-43-8P; 728041-44-9P Role: SPN (Synthetic preparation), PREP (Preparation) (synthesis of oxazoles and peptides having alpha -hydroxy-beta -amino acid component by diastereoselective Passerini reaction)
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