Keywords
acetals
acyliminium cation
amidoalkylation
Kabachnik�Fields reaction.
phospha lactone
phosphinic pseudopeptides
phosphonous carboxylic diacids
Abstract
The use of free phosphonous carboxylic diacids in three-component carbamate version of the Kabachnik--Fields reaction in acetyl chloride medium allows introducing acetals into the reaction sphere to result in phosphinic peptides. The employment of low-stable and functionally substituted aldehydes in the form of acetals provides phosphinic peptides that are difficult to obtain by other methods.
Funders
Russian Science Foundation
23-23-00158
References
.
Sheldrick G.M.
Acta crystallographica. Section C, Structural chemistry,
2015
.
Mucha A.
Molecules,
2012
.
Matziari M., Bauer K., Dive V., Yiotakis A.
Journal of Organic Chemistry,
2008
.
Mechanism of Phosphorus–Carbon Bond Formation in the Amidoalkylation of Phosphonous Carboxylic Acids
Dmitriev M.E., Golovash S.R., Borodachev A.V., Ragulin V.V.
Journal of Organic Chemistry,
2020
.
Hori M., Nishida K.
Cardiovascular Research,
2008
.
Dmitriev M.E., Ragulin V.V.
Tetrahedron Letters,
2012
.
Palatinus L., Chapuis G.
Journal of Applied Crystallography,
2007
.
Mucha A., Kafarski P., Berlicki Ł.
Journal of Medicinal Chemistry,
2011
.
Pirard B., Matter H.
Journal of Medicinal Chemistry,
2005
.
Dmitriev M.E., Ragulin V.V.
Russian Journal of General Chemistry,
2012
.
Rozhko L.F., Ragulin V.V.
Amino Acids,
2005
.
Dive V., Georgiadis D., Matziari M., Makaritis A., Beau F., Cuniasse P., Yiotakis A.
Cellular and Molecular Life Sciences,
2004
.
Talma M., Maślanka M., Mucha A.
Bioorganic and Medicinal Chemistry Letters,
2019
.
Dmitriev M.E., Ragulin V.V.
Tetrahedron Letters,
2010
.
Georgiadis D., Dive V.
Topics in Current Chemistry,
2014
.
Golovash S.R., Borodachev A.V., Dmitriev M.E., Ragulin V.V.
Mendeleev Communications,
2023