Petasis反應

Petasis反應（Petasis reaction），是胺、醛與烯基／芳基硼酸反應生成取代胺類的反應。^[1]^[2]^[3]

此反應可看作是Mannich反應的烷基硼酸變體。它提供了除還原胺化反應以外一種合成取代胺類的方法。

應用

利用發散合成法製備多官能團產物：^[4] ^[5]

Petasis反應實例 (Kumagai等)

^ Petasis, N. A.; Akritopoulou, I. The boronic acid mannich reaction: A new method for the synthesis of geometrically pure allylamines. Tetrahedron Lett. 1993, 34: 583–586. doi:10.1016/S0040-4039(00)61625-8.
^ Petasis, N. A.; Zavialov, I. A. A New and Practical Synthesis of -Amino Acids from Alkenyl Boronic Acids. J. Am. Chem. Soc. 1997, 119: 445–446. doi:10.1021/ja963178n.
^ Petasis, N. A.; Zavialov, I. A. Highly Stereocontrolled One-Step Synthesis of anti-β-Amino Alcohols from Organoboronic Acids, Amines, and α-Hydroxy Aldehydes. J. Am. Chem. Soc. 1998, 120: 11798–11799. doi:10.1021/ja981075u.
^ Naoya Kumagai, Giovanni Muncipinto, Stuart L. Schreiber. Short Synthesis of Skeletally and Stereochemically Diverse Small Molecules by Coupling Petasis Condensation Reactions to Cyclization Reactions. Angewandte Chemie International Edition. 2006, 45: 3635–3638. doi:10.1002/anie.200600497.
^ 反應物：L-苯基乳酸、丙酮、L-苯基丙氨酸甲酯和一個烷基硼酸。反應在乙醇中室溫下進行，非對映體過量百分數99％。