Study On The PET-catalyzed Cycloaddition Reaction Of Spiro[indole-3,2’-epoxide]-2-ones With Olefins And The Rearrangement Reaction Of The Epoxides

This thesis is mainly focused on the photoinduced electron transfer (PET)-catalyzed [3+2] cycloaddition reaction of spiro[indole-3,2’-epoxide]-2-ones with electron-rich olefins and the rearrangement reaction of the epoxide in the presence of photocatalyst or Lewis acid.It consists of two parts.The first part is the summary of PET-catalyzed reactions and the photosensitized or acid-catalyed rearrangement reactions of the epoxides. The mechanism of the photoinduced electron transfer reaction, the variety of photoinduced electron transfer reactions and the application in organic synthesis have been reviewed. Especially the PET-catalyzed cycloaddition reactions of epoxides are introduced. Then the ring-opening and rearrangement reactions of epoxides catalyzed by Lewis acid, bases, metal catalysts and photocatalyst have been recommended.The second part is the report of my investigation works.(1) The TPT-catalyzed ring opening of substituted spiro[indole-3,2’-epoxide]-2-ones via Cβ-0bond cleavage and subsequent cycloaddition with olefins. An efficient procedure for synthesis of spiro[furan-3,3’-indolin]-2-ones and dispiro[cycloalkane-1,2’-furan-3’,3μ-indolin]-2"-ones in high yields and stereoselectivity by PET-catalyzed [3+2] reactions has been established in my work.(2) The rearrangement of spiro[indole-3,2’-epoxide]-2-ones catalyzed by the photosensitizers and Lewis acid.3,3-Dialkyl-2,3-quinolindiones can be obtained by Ca-O bond cleavage and subsequent rearrangement reaction in the presence of SnCl4differently,3-alkyl-3-acyl-2-indolones have been obtained in high yields by the ring opening and rearrangement of these2-indolone epoxides using benzophenone as a sensitizer via selective Cβ-0bond cleavage.