Catalytic Enantioselective Synthesis of Azepine-Fused Planar-Chiral Ferrocenes by Pt-Catalyzed Cycloisomerization

Mamoru Ito, Moeka Okamura, Kyalo Stephen Kanyiva, Takanori Shibata

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

Enantioselective synthesis of azepine-fused planar-chiral ferrocenes was achieved by the chiral cationic Pt-catalyzed intramolecular cycloisomerization of N-propargyl-2-ferrocenylanilines. A mechanistic study using an N-allenyl analogue indicated that the reaction proceeded selectively in a 7-exo-dig manner along with isomerization of the exo-olefin moiety. A methanesulfonylamino tether was crucial for selective cycloisomerization. This is the first example of the enantioselective synthesis of heteropin-fused planar-chiral ferrocenes.

Original languageEnglish
Pages (from-to)4029-4035
Number of pages7
JournalOrganometallics
Volume38
Issue number20
DOIs
Publication statusPublished - 2019 Oct 28

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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