title: The homo-PADAM protocol: stereoselective and operationally simple synthesis of α-oxo- or α-hydroxy-γ-acylaminoamides and chromanes.
abstract: A straightforward and fully stereoselective synthesis of a new class of peptidomimetics, that is α-oxo-γ-acylaminoamides, was achieved starting from various benzaldehydes by a sequence of 1) an asymmetric organocatalytic Mannich reaction, 2) a Passerini multicomponent reaction, 3) an amine deprotection-acyl migration protocol, and 4) a final oxidation. The whole sequence can be performed without purification of the intermediates and represents the first example of a homo-Passerini-amine deprotection-acyl migration (PADAM) strategy. Highly stereoselective reduction of the α-oxo-γ-acylaminoamides afforded α-hydroxy-γ-acylaminoamides as well. In some cases both diastereomers were obtained by simply changing the reducing agent. Finally, starting from protected salicylaldehyde, the same sequence, followed by a Mitsunobu cyclization, afforded highly substituted chromanes.
authors: Department of Chemistry and Industrial Chemistry, University of Genova via Dodecaneso, 31, 16146 Genova, Italy.
authors: Fabio
authors: F
authors: Morana
authors: Andrea
authors: A
authors: Basso
authors: Renata
authors: R
authors: Riva
authors: Valeria
authors: V
authors: Rocca
authors: Luca
authors: L
authors: Banfi