User:Rifleman 82/Petasis reaction

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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
The Petasis reaction

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

In one application the Petasis reaction is used for quick access to a multifunctional scaffold for divergent synthesis.[4][5]

Petasis reaction example (Kumagai et al.)
Petasis reaction example (Kumagai et al.)

See also

References

  1. ^ 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)
  2. ^ 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)
  3. ^ 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)
  4. ^ 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)
  5. ^ 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%.