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Synthesis of decahydropyrrolo[2,1,5-cd]indolizine through consecutive [2 + 3] cycloadditions and 6-exo-trig cyclization
Authors:Cui Peipei  Xu Liang  Shi Zhangjie  Gan Liangbing
Institution:Beijing National Laboratory for Molecular Sciences, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.
Abstract:Azomethine ylide formed from glycine methyl ester and cinnamaldehyde adds to N-phenylmaleimide to form pyrrolidine derivative, further treatment of which with cinnamaldehyde and N-phenylmaleimide affords the second 2 + 3] cycloaddition adduct, a pyrrolizine derivative with two styrenyl groups at the 3,5-positions. Addition of ICl to the pyrrolizine derivative results in the 6-exo-trig cyclization of the styrenyl groups to form a cycl3.2.2]azine derivative. The reactions are highly stereoselective affording 11 chiral carbons in three steps. The structure of the cycl3.2.2]azine derivative was determined by single-crystal X-ray analysis.
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