Synthesis and Resolution of Substituted [5]Carbohelicenes

Kazuteru Usui, Kosuke Yamamoto, Takashi Shimizu, Mieko Okazumi, Biao Mei, Yosuke Demizu, Masaaki Kurihara, Hiroshi Suemune

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Three types of racemic [5]helicenyl acetates (1a, 2, and 3a) were synthesized. The synthesis of 2 was achieved by regioselective oxidation using o-iodoxybenzoic acid. The enzymatic kinetic resolution of 1a-3a was studied. The conversion with the highest rate and ee was obtained using 1a as the substrate and lipase Amano PS-IM as the enzyme. The two enantiomers of 1-[5]helicenol 3b were separated using (1S)-10-camphorsulfonyl chloride as the chiral resolving agent.

Original languageEnglish
Pages (from-to)6502-6508
Number of pages7
JournalJournal of Organic Chemistry
Volume80
Issue number12
DOIs
Publication statusPublished - Jun 19 2015

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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