Petasis反應

Petasis反應(Petasis reaction),是烯基芳基硼酸反應生成取代胺類的反應。[1][2][3]


Petasis反應
Petasis反應


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)

參見

參考資料

  1. ^ 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. 
  2. ^ 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. 
  3. ^ 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. 
  4. ^ 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. 
  5. ^ 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%。