Petasis反应

Petasis反应（Petasis reaction），是胺、醛与烯基／芳基硼酸反应生成取代胺类的反应。^[1]^[2]^[3]

此反应可看作是Mannich反应的烷基硼酸变体。它提供了除还原胺化反应以外一种合成取代胺类的方法。

应用

利用发散合成法制备多官能团产物：^[4] ^[5]

Petasis反应实例 (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.
^ 反应物：L-苯基乳酸、丙酮、L-苯基丙氨酸甲酯和一个烷基硼酸。反应在乙醇中室温下进行，非对映体过量百分数99％。