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PETASIS BORONIC ACID-MANNICH REACTION

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Presentation on theme: "PETASIS BORONIC ACID-MANNICH REACTION"— Presentation transcript:

1 PETASIS BORONIC ACID-MANNICH REACTION
WZQ NIBS 1

2 PETASIS BORONIC ACID-MANNICH REACTION
The Petasis reaction (alternatively called the Petasis borono–Mannich (PBM) reaction) is the chemical reaction of an amine, aldehyde, and vinyl- or aryl-boronic acid to form substituted amines. Mannich reaction : NIBS 1

3 PETASIS BORONIC ACID-MANNICH REACTION
Mechanism The reaction does not go through intermediate A. Both intermediate B and C can promote the formation of the product. Most likely, the reaction proceeds through intermediate C, where the hydroxyl group attacks the electrophilic boron leading to an “ate”-complex. Subsequent vinyl transfer provides the allylic amine along with the boronic acid sideproduct. NIBS 1

4 PETASIS BORONIC ACID-MANNICH REACTION
Mechanism  Petasis, N.A. (2005). Zhu, J.; Bienayme, H., eds. Multicomponent Reactions. Wiley-VCH. pp. 199–223. doi: / ch7 NIBS 1

5 PETASIS BORONIC ACID-MANNICH REACTION
Synthetic Applications: NIBS 1

6 PETASIS BORONIC ACID-MANNICH REACTION
Synthetic Applications: NIBS 1

7 PETASIS BORONIC ACID-MANNICH REACTION
Synthetic Applications: Lou, S.; Schaus, S.E. (2008). "Asymmetric petasis reactions catalyzed by chiral biphenols".  J. Am. Chem. Soc. 130 (22): 6922–6923. doi: /ja   NIBS 1

8 PETASIS BORONIC ACID-MANNICH REACTION
Synthetic Applications:  Han, W.-Y.; Wu, Z.-J.; Zhang, X.-M.; Yuan, W.-C. (2012), "Enantioselective Organocatalytic Three-Component Petasis Reaction among Salicylaldehydes, Amines, and Organoboronic Acids", Org. Lett., ASAP (4): 976–979, doi: /ol203109a NIBS 1


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