1448797-34-9Relevant academic research and scientific papers
The homo-PADAM protocol: Stereoselective and operationally simple synthesis of α-oxo- or α-hydroxy-γ-acylaminoamides and chromanes
Morana, Fabio,Basso, Andrea,Riva, Renata,Rocca, Valeria,Banfi, Luca
, p. 4563 - 4569 (2013/04/24)
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. Copyright
