Hübner Sandra, Jiao Haijun, Michalik Dirk, Neumann Helfried, Klaus Stefan, Strübing Dirk, Spannenberg Anke, Beller Matthias
Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Rostock, Germany.
Chem Asian J. 2007 Jun 4;2(6):720-33. doi: 10.1002/asia.200600428.
Chiral N-dienyl lactams are crucial building blocks for the synthesis of complex organic compounds. However, their generation is rather challenging. This paper reports on a highly efficient and diastereoselective multicomponent methodology utilizing chiral amides, aldehydes, and dienophiles (AAD reaction). The three components readily react under in situ generation of chiral N-dienyl lactams which undergo a subsequent Diels-Alder reaction. Different chiral amides have been employed in the standard protocol delivering yields up to 94%, and selectivities up to 90% de. Moreover, DFT calculations were performed to explain the obtained selectivities.
手性N-二烯基内酰胺是合成复杂有机化合物的关键构建单元。然而，它们的生成颇具挑战性。本文报道了一种利用手性酰胺、醛和亲双烯体的高效非对映选择性多组分方法（AAD反应）。这三种组分在手性N-二烯基内酰胺原位生成的条件下很容易发生反应，随后进行狄尔斯-阿尔德反应。在标准方案中使用了不同的手性酰胺，产率高达94%，非对映选择性高达90%。此外，还进行了密度泛函理论计算以解释所获得的选择性。
