Wang, ShixinWang, Mei-XiangWang, De-XianZhu, Jieping2010-11-252010-11-252010-11-25200710.1002/ejoc.200700340https://infoscience.epfl.ch/handle/20.500.14299/58427Stannous chloride efficiently catalyzes condensations between alpha -isocyanoacetamides C==NCHRCOR1 (I, R = H, PhCH2; R1 = N-morpholinyl, Et2N) and a variety of aldehydes to afford the corresponding 5-amino-2-(1-hydroxyalkyl)oxazoles II (R2 = Et, n-C6H13, Me2CH, cyclohexyl, tert-Bu, COOEt, Ph, etc.) in good to excellent yields. The [Sn-(R)-Ph-PyBox](OTf)2-catalyzed reaction between I (R = PhCH2; R1 = N-morpholinyl) and 2-(benzyloxy)acetaldehyde shows an isoinversion effect, with the max. enantiomeric excess of oxazole II (R2 = PhCH2OCH2) (80%) obtained at -40 Deg. [on SciFinder (R)]Stereoselective synthesis (Lewis acid-catalyzed prepn. of 5-amino-2-(1-hydroxyalkyl)oxazoles by condensation of alpha -isocyanoacetamides with aldehydes and extension to asym. Passerini-type addn. using [Sn-(R)-Ph-PyBox](OTf)2 catalyst); Aldehydes; Isocyanides Role: RCT (Reactant)RACT (Reactant or reagent) (Lewis acid-catalyzed prepn. of 5-amino-2-(1-hydroxyalkyl)oxazoles by condensation of alpha -isocyanoacetamides with aldehydes and extension to asym. Passerini-type addn. using [Sn-(R)-Ph-PyBox](OTf)2 catalyst); Cyclocondensation reaction; Cyclocondensation reaction catalysts (Passerini-type; Lewis acid-catalyzed prepn. of 5-amino-2-(1-hydroxyalkyl)oxazoles by condensation of alpha -isocyanoacetamides with aldehydes and extension to asym. Passerini-type addn. using [Sn-(R)-Ph-PyBox](OTf)2 catalyst); Cyclocondensation reaction catalysts (stereoselective Passerini-type; Lewis acid-catalyzed prepn. of 5-amino-2-(1-hydroxyalkyl)oxazoles by condensation of alpha -isocyanoacetamides with aldehydes and extension to asym. Passerini-type addn. using [Sn-(R)-Ph-PyBox](OTf)2 catalyst); Cyclocondensation reaction (stereoselectivePasserini-type; Lewis acid-catalyzed prepn. of 5-amino-2-(1-hydroxyalkyl)oxazoles by condensation of alpha -isocyanoacetamides with aldehydes and extension to asym. Passerini-type addn. using [Sn-(R)-Ph-PyBox](OTf)2 catalyst)isocyanoacetamide aldehyde tin addn Passerini asym; enantioselective Passerini cyclocondensation tin chiral bidentate ligand; oxazole amino prepn stannous chloride catalyst; aminooxazole prepn stannous chloride catalystAsymmetric Lewis acid catalyzed addition of isocyanides to aldehydes. Synthesis of 5-amino-2-(1-hydroxyalkyl)oxazolestext::journal::journal article::research article