Solvent-Controlled Diastereodivergent Synthesis of Hexahydropyrrolo[2,1-a]isoquinolines through Pd/C-Catalyzed
Ji-Chao Lu1, Hao Bai1, Yue-He Huang1
1School of Chemistry and Chemical Engineering, Hefei University of Technology, 193 Tunxi Road, Hefei 230009, China.
Abstract:
A Pd/C-catalyzed dehydrogenative [3 + 2] cycloaddition is described for the diastereoswitchable synthesis of hexahydropyrrolo[2,1-a]isoquinolines by altering solvents. The reaction proceeds through a sequential Pd/C-catalyzed dehydrogenative formation of azomethine ylides from tetrahydroisoquinoline acetates and 1,3-dipolar cycloaddition with 2-nitroethenylbenzenes. This method displayed tunable diastereoselectivity, a broad substrate scope and good functional group compatibility. Moreover, a gram-scale synthesis and selective reductive or oxidative transformations of the product further demonstrate the utility of this methodology.
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