Cuny, GuylaineGamez-Montano, RocioZhu, Jieping2010-11-252010-11-252010-11-25200410.1016/j.tet.2004.03.084https://infoscience.epfl.ch/handle/20.500.14299/58481The 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)]Addition reaction (Passerinidiastereoselective; synthesis of oxazoles and peptides having alpha -hydroxy-beta -amino acid component by diastereoselective Passerini reaction); Stereoselective synthesis (synthesis of oxazoles and peptides having alpha -hydroxy-beta -amino acid component by diastereoselective Passerini reaction); Aldehydes; Isocyanides; Ketones Role: RCT (Reactant)RACT (Reactant or reagent) (synthesis of oxazoles and peptides having alpha -hydroxy-beta -amino acid component by diastereoselective Passerini reaction); Peptides Role: SPN (Synthetic preparation)PREP (Preparation) (synthesis of oxazoles and peptides having alpha -hydroxy-beta -amino acid component by diastereoselective Passerini reaction)diastereoselective Passerini reaction carbonyl isocyano amide synthesis oxazole peptide; norstatine peptide prepn diastereoselective Passerini reactiontext::journal::journal article::research article