Petasis reaction


Petasis reaction

The Petasis reaction is the chemical reaction of an amine, aldehyde, and vinyl- or aryl-boronic acid to form substituted amines. [cite journal | author = Petasis, N. A.; Akritopoulou, I. | journal = Tetrahedron Lett. | year = 1993 | volume = 34 | pages = 583–586 | doi = 10.1016/S0040-4039(00)61625-8 | title = The boronic acid mannich reaction: A new method for the synthesis of geometrically pure allylamines] [cite journal | author = Petasis, N. A.; Zavialov, I. A. | journal = J. Am. Chem. Soc. | year = 1997 | volume = 119 | pages = 445–446 | title = A New and Practical Synthesis of -Amino Acids from Alkenyl Boronic Acids | doi = 10.1021/ja963178n] [cite journal | author = Petasis, N. A.; Zavialov, I. A. | title = Highly Stereocontrolled One-Step Synthesis of anti-β-Amino Alcohols from Organoboronic Acids, Amines, and α-Hydroxy Aldehydes| | journal = J. Am. Chem. Soc. | year = 1998 | volume = 120 | pages = 11798–11799 | doi = 10.1021/ja981075u]

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. [cite journal | author = Naoya Kumagai, Giovanni Muncipinto, Stuart L. Schreiber | journal = Angewandte Chemie International Edition | year = 2006 | volume = 45 | pages = 3635–3638 | doi = 10.1002/anie.200600497 | title = Short Synthesis of Skeletally and Stereochemically Diverse Small Molecules by Coupling Petasis Condensation Reactions to Cyclization Reactions] [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%."]

ee also

*Mannich reaction
*Suzuki reaction

References


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