Construction of Chiral-Fused Tricyclic γ‑Lactams via a trans-Perhydroindolic Acid-Catalyzed Asymmetric Domino Reaction

An asymmetric domino
reaction was developed utilizing readily available
cyclic α-dehydroamino ketones and aldehydes, which when subjected
a 2-iodoxybenzoic acid (IBX)-mediated oxidation gives pyrrolidinone-containing
tricyclic derivatives. trans-Perhydroindolic acid
proved to be an efficient organocatalyst in this reaction (up to 94%
yield, 99% ee, and >20:1 dr). The product could be conveniently
converted
to synthetically useful intermediates via simple transformations.
A possible stereocontrolled process has been suggested according to
X-ray crystallography studies.

采用易得的环状α-脱氢氨基酮和醛类化合物开发的非对称性多米诺反应，经2-碘氧基苯甲酸（IBX）介导的氧化反应后，可获得含吡咯烷酮的三环衍生物。反式-四氢吲哚酸在此次反应中表现出了高效的有机催化剂特性（最高产率为94%，ee值为99%，dr值大于20:1）。该产物可通过简便的转化过程转化为合成上具有重要价值的中间体。根据X射线晶体学研究，提出了一种可能的立体控制过程。