title: Synthesis of decahydropyrrolo[2,1,5-cd]indolizine through consecutive [2 + 3] cycloadditions and 6-exo-trig cyclization.
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 cycl[3.2.2]azine derivative. The reactions are highly stereoselective affording 11 chiral carbons in three steps. The structure of the cycl[3.2.2]azine derivative was determined by single-crystal X-ray analysis.
authors.affiliation: Beijing National Laboratory for Molecular Sciences, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.
authors.forename: Peipei
authors.initials: P
authors.lastname: Cui
authors.forename: Liang
authors.initials: L
authors.lastname: Xu
authors.forename: Zhangjie
authors.initials: Z
authors.lastname: Shi
authors.forename: Liangbing
authors.initials: L
authors.lastname: Gan