User:Rifleman 82/Petasis reaction
| Rifleman 82/Petasis reaction | |
|---|---|
| Substrate | |
| Reagent(s) | |
| Reactants | boronic acids, amines, aldehydes |
| Catalyst | {{{catalyst}}} |
| Product | substituted amines |
| Discoverer | N. A. Petasis ({{{year}}}) |
| Similar reactions | Mannich reaction |
The Petasis reaction is the chemical reaction of an amine, aldehyde, and vinyl- or aryl-boronic acid to form substituted amines.[1][2][3]
The Petasis reaction can be viewed as a boronic acid equivalent of the Mannich reaction, and is often used as an alternative to the reductive amination reaction.
Applications
[edit]In one application the Petasis reaction is used for quick access to a multifunctional scaffold for divergent synthesis.[4][5]
See also
[edit]References
[edit]- ^ Petasis, N. A.; Akritopoulou, I. (1993). "The boronic acid mannich reaction: A new method for the synthesis of geometrically pure allylamines". Tetrahedron Lett. 34: 583–586. doi:10.1016/S0040-4039(00)61625-8.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Petasis, N. A.; Zavialov, I. A. (1997). "A New and Practical Synthesis of -Amino Acids from Alkenyl Boronic Acids". J. Am. Chem. Soc. 119: 445–446. doi:10.1021/ja963178n.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Petasis, N. A.; Zavialov, I. A. (1998). "Highly Stereocontrolled One-Step Synthesis of anti-β-Amino Alcohols from Organoboronic Acids, Amines, and α-Hydroxy Aldehydes". J. Am. Chem. Soc. 120: 11798–11799. doi:10.1021/ja981075u.
{{cite journal}}: Cite has empty unknown parameter:|1=(help)CS1 maint: multiple names: authors list (link) - ^ Naoya Kumagai, Giovanni Muncipinto, Stuart L. Schreiber (2006). "Short Synthesis of Skeletally and Stereochemically Diverse Small Molecules by Coupling Petasis Condensation Reactions to Cyclization Reactions". Angewandte Chemie International Edition. 45: 3635–3638. doi:10.1002/anie.200600497.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ The reactants are the lactol derived from L-phenyl-lactic acid and acetone, l-phenylalanine methyl ester and a boronic acid. The reaction takes place in ethanol at room temperature with diastereomeric excess 99%.