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

18 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

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Enantiomers
Lipase
Chlorides
Acetates
Oxidation
Kinetics
Substrates
Enzymes
o-iodoxybenzoic acid

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Usui, K., Yamamoto, K., Shimizu, T., Okazumi, M., Mei, B., Demizu, Y., ... Suemune, H. (2015). Synthesis and Resolution of Substituted [5]Carbohelicenes. Journal of Organic Chemistry, 80(12), 6502-6508. https://doi.org/10.1021/acs.joc.5b00759

Synthesis and Resolution of Substituted [5]Carbohelicenes. / Usui, Kazuteru; Yamamoto, Kosuke; Shimizu, Takashi; Okazumi, Mieko; Mei, Biao; Demizu, Yosuke; Kurihara, Masaaki; Suemune, Hiroshi.

In: Journal of Organic Chemistry, Vol. 80, No. 12, 19.06.2015, p. 6502-6508.

Research output: Contribution to journalArticle

Usui, K, Yamamoto, K, Shimizu, T, Okazumi, M, Mei, B, Demizu, Y, Kurihara, M & Suemune, H 2015, 'Synthesis and Resolution of Substituted [5]Carbohelicenes', Journal of Organic Chemistry, vol. 80, no. 12, pp. 6502-6508. https://doi.org/10.1021/acs.joc.5b00759
Usui K, Yamamoto K, Shimizu T, Okazumi M, Mei B, Demizu Y et al. Synthesis and Resolution of Substituted [5]Carbohelicenes. Journal of Organic Chemistry. 2015 Jun 19;80(12):6502-6508. https://doi.org/10.1021/acs.joc.5b00759
Usui, Kazuteru ; Yamamoto, Kosuke ; Shimizu, Takashi ; Okazumi, Mieko ; Mei, Biao ; Demizu, Yosuke ; Kurihara, Masaaki ; Suemune, Hiroshi. / Synthesis and Resolution of Substituted [5]Carbohelicenes. In: Journal of Organic Chemistry. 2015 ; Vol. 80, No. 12. pp. 6502-6508.
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