Categories: Synthesis of N-Heterocycles >
Synthesis of 2,3-dihydro-4-pyridones
The aza Diels-Alder reaction of an in situ generated novel iododiene works well with aryl- and benzyl-N-substituted imines. Moderate diastereoselectivities can be obtained using simple α-methylbenzyl chiral imines.
C. Timmons, A. Kattuboina, L. McPherson, J. Mills, G. Li, Tetrahedron, 2005, 61, 11837-11842.
Imidazolinium salts are capable of catalysing an aza-Diels-Alder reaction with a range of imines and Danishefsky's diene, leading to the desired products in good to excellent yields.
V. Jurcik, R. Wilhelm, Org. Biomol. Chem., 2005, 3, 239-244.
An enantiospecific syntheses of pyridinones from amino acids via a gold-catalyzed strategy allows excellent stereocontrol during cyclization. This approach provides a straightforward tool for further synthetic applications toward piperidines.
N. Gouault, M. Le Roch, A. Cheignon, P. Uriac, M. David, Org. Lett., 2011, 13, 4371-4373.
A gold-catalyzed cyclization of β-amino-ynone intermediates and halodeauration process enables a rapid and efficient one-step halopyridone synthesis.
K. H. Nguyen, S. Tomasi, M. Le Roch, L. Toupet, J. Renault, P. Uriac, N. Gouault, J. Org. Chem., 2013, 78, 7809-7815.