Passerini Reaction

M. Passerini, Gazz. Chim. Ital. 51, 126, 181 (1921).

Formation of α-hydroxycarboxamides on treatment of an isonitrile with a carboxylic acid and an aldehyde or ketone:



Synthetic applications: J. R. Falck, S. Manna, Tetrahedron Letters 22, 619 (1981); R. Bossio et al., Synthesis 1993, 783. Modifications: W. E. Lumma, J. Org. Chem. 46, 3668 (1981); T. Carofiglio et al., Organometallics 12, 2726 (1993); for stereoselectivity: H. Bock, I. Ugi, J. Prakt. Chem. 339, 385 (1997); for combinatorial chemistry; H. Bienaymé, Tetrahedron Letters 39, 4255 (1998); S. W. Kim Tetrahedron Letters 39, 7031 (1998). Reviews: I. Ugi, Angew. Chem. Int. Ed. 1, 8 (1962); I. Ugi et al., in Isonitrile Chemistry (Academic Press, New York, 1971) pp 133-143; I. Ugi, et al., Comp. Org. Syn. 2, 1083-1087 (1991).