Passerini

Alessandri, Atti accad. Lincei 24 II 199 (1915) Alessandri and Passerini, Gazz. chim. ital. 51, I 277 (1921). 

L. Alessandri and M. Passerini, Oazz. Chim. Ital. 51, 262 (1921) Chem. 

Like the Strecker synthesis, the Ugi reaction also involves a nucleophilic addition to an imine as the crucial step in which the stereogenic center of an a-amino acid derivative is formed4. The Ugi reaction, also denoted as a four-component condensation (A), is related to the older Passerini reaction5 (B) in an analogous fashion as the Strecker synthesis is to cyanohydrin formation. In both the Ugi and the Passerini reaction, an isocyanide takes the role of cyanide. 

When an isocyanide is treated with a carboxylic acid and an aldehyde or ketone, an a-acyloxy amide is prepared. This is called the Passerini reaction. The following mechanism has been postulated ... 

Gambacorti-Passerini C., Mologni L, Bertazzoli C., le Coutre P., Marchesi E., Grignani F., Nielsen P.E. In vitro transcription and translation inhibition by anti-promyelocytic leukemia (PML)/re-tinoic acid receptor-alpha and anti-PML peptide nucleic acid. Blood 1996 88 1411-1417. 

Mologni L., Lecoutre P., Nielsen P.E., Gambacorti-Passerini G. Additive anti-sense effects of different PNAs on the in vitro translation of the PML/RAR-alpha gene. Nucleic Acids Res. 1998 26 1934-1938. 

Mologni L., Marches E., Nielsen P.E., Gai4BACOrti-Passerini C. Inhibition of promyelocytic leukemia (PML)/retinoic acid receptor-alpha and PML expression in acute promyelocytic leukemia cells by anti-PML peptide nucleic acid. Cancer Res. 2001 61 5468-5473. 

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