Tanaka Katsunori, Katsumura Shigeo
School of Science and Technology, Kwansei Gakuin University, Gakuen 2-1, Sanda, Hyogo 669-1337, Japan.
J Am Chem Soc. 2002 Aug 21;124(33):9660-1. doi: 10.1021/ja026464+.
Highly stereoselective asymmetric 6pi-azaelectrocyclization was achieved with generality, based on the reaction between the (E)-3-carbonyl-2,4,6-trienal compounds and the (-)-7-alkyl-cis-1-amino-2-indanol derivatives as the effective novel chiral amines. Furthermore, the chiral auxiliaries of the cyclized products obtained were efficiently removed by the novel manganese dioxide oxidation under remarkably mild conditions, and the method was successfully applied to the formal synthesis of optically active 20-epiuleine.
基于（E）-3-羰基-2,4,6-三烯醛化合物与（-）-7-烷基-顺式-1-氨基-2-茚醇衍生物作为有效的新型手性胺之间的反应，实现了具有普遍性的高度立体选择性不对称6π-氮杂电环化反应。此外，通过新型二氧化锰氧化反应，在非常温和的条件下有效地除去了所得环化产物的手性助剂，该方法成功应用于光学活性20-表优列伊内的形式合成。
