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Please login to access the full content or check if you have access via Method 8: Nucleophilic Addition of Boronic Acids to Imines (The Petasis Reaction)

DOI: 10.1055/sos-SD-036-00701

Bingham, M. J.; Greaney, M. F.Science of Synthesis, (200836995.

The three-component coupling of boronic acids 44, aldehydes 45, and amines 46 is a powerful approach to the synthesis of functionalized amines 47 (Scheme 19). The reaction, introduced by Petasis in 1997, is usually carried out with glyoxylic or α-hydroxy aldehyde components that contain a coordinating functional group adjacent to the carbonyl group.[‌151‌,‌152‌] This method produces the product subclass in a single simple step, and many of the starting materials are commercially available. In addition, the reaction is highly diastereoselective for anti-β-amino alcohols (e.g., 48) and, in cases where the α-hydroxy aldehyde is employed as a single enantiomer, proceeds without detectable racemization to produce optically pure products.

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