Petasis reaction

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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.

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

See also

References

  1. Petasis, N. A.; Akritopoulou, I. Tetrahedron Lett. 1993, 34, 583–586.
  2. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445–446. Abstract
  3. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798-Abstract
  4. Naoya Kumagai, Giovanni Muncipinto, Stuart L. Schreiber Angewandte Chemie International Edition 2006, 45,3635 - 3638 Abstract
  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%.

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