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.<ref>Petasis, N. A.; Akritopoulou, I. ''[[Tetrahedron Lett.]]'' '''1993''', ''34'', 583–586.</ref><ref>Petasis, N. A.; Zavialov, I. A. ''[[J. Am. Chem. Soc.]]'' '''1997''', ''119'', 445–446. ({{DOI|10.1021/ja963178n}})</ref><ref>Petasis, N. A.; Zavialov, I. A. ''[[J. Am. Chem. Soc.]]'' '''1998''', ''120'', 11798-11799. ({{DOI|10.1021/ja981075u}})</ref>
[[Image:Petasis_Reaction_Scheme.png|center|450px|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]].<ref>Naoya Kumagai, Giovanni Muncipinto, Stuart L. Schreiber [[Angewandte Chemie International Edition]] '''2006''', ''45'',3635 - 3638 [http://dx.doi.org/10.1002/anie.200600497 Abstract]</ref><ref>''The reactants are the [[lactol]] derived from [[lactic acid|L-phenyl-lactic acid]] and [[acetone]], [[alanine|l-phenylalanine methyl ester]] and a [[boronic acid]]. The reaction takes place in [[ethanol]] at [[room temperature]] with [[diastereomeric excess]] 99%.''</ref>
[[Image:PetasisReaction.png|center|700px|Petasis reaction example (Kumagai et al.)]]
==References==
{{Reflist}}
==See also==
*[[Mannich reaction]]
*[[Suzuki reaction]]
[[Category:Multiple component reactions]]
[[Category:Substitution reactions]]
[[Category:Name reactions]]