Synthesis of pyrrolidine-fused [34]- and [36]octaphyrins via 1,3-dipolar cycloaddition

Hiroshi Hata; Yiho Kamimura; Hiroshi Shinokubo; Atsuhiro Osuka

doi:10.1021/ol060067c

Synthesis of pyrrolidine-fused [34]- and [36]octaphyrins via 1,3-dipolar cycloaddition

Org Lett. 2006 Mar 16;8(6):1169-72. doi: 10.1021/ol060067c.

Authors

Hiroshi Hata¹, Yiho Kamimura, Hiroshi Shinokubo, Atsuhiro Osuka

Affiliation

¹ Department of Chemistry, Graduate School of Science, Kyoto University and PRESTO & CREST, Japan Science and Technology Agency (JST), Kyoto 606-8502, Japan.

PMID: 16524295
DOI: 10.1021/ol060067c

Abstract

[reaction: see text] The utility of expanded porphyrins as a dipolarophile in cycloaddition reactions has been investigated. The 1,3-dipolar cycloaddition of meso-octakis(pentafluorophenyl)[36]octaphyrin(1.1.1.1.1.1.1.1) with an azomethine ylide provides mono- and bis-pyrrolidine-fused octaphyrins regio- and stereoselectively. Treatment of the cycloadduct with MnO(2) afforded [34]octaphyrin quantitatively.