Synthesis Of Pyrrolo[1,2-a]Indoles By Michael-aldol-1,5-hydrogen Migration Cascade Reactios And Application Of Chiral Amine In N-heterocyclic Carbene

This thesis is composed of three parts:(1) The ring of pyrrolo[1,2-a]indole is an important skeleton of many natural products, such as members of the mitomycin family and isatisine A. These compounds often display special biological activities. Furthermore, they are also used as intermediates for the synthesis of some natural products and complex drug molecules. In this chapter, the methods for synthesis of the pyrrolo[1,2-a]indole skeleton is summarized.(2) We have developed an efficient method for the synthesis of 9H-pyrrolo[1,2-a]indol-2-methanone derivatives by Michael-aldol-1,5-hydrogen migration cascade reactions of substituted terminal olefinic ketones with indole-2-carbaldehydes in the presence of DBU. The desired products were obtained in moderate to good yields (up to 92%) under mild reaction conditions.(3) Two aliphatic primary amines, which containing aromatic group, alicyclic group and isobutyl groups and with large steric hindrance, were synthesized from nitrile by three steps. One of the primary amine was resoluted by L-(+)-tartaric acid and the chiral amine was obtained in>99% ee. Furthermore, two new N-heterocyclic carbenes precursor was synthesized from the chiral amine.