Enantioselective C - C Bond Formation Enhanced by Self-Assembly of Achiral Surfactants

Fumihiko Iwasaki, Keishi Suga, Yukihiro Okamoto, Hiroshi Umakoshi

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

The use of achiral surfactant assemblies as a reaction platform for an alkylation reaction resulted in a high enantiomeric excess. Dilauryldimethylammonium bromide (DDAB) vesicles were modified with cholesterol to promote alkylation of N-(diphenylmethylene)glycine tert-butyl ester (DMGBE) with benzyl bromide, resulting in high conversion (∼90%) and high enantioselectivity (up to 80%). The R-enantiomer was formed on using the DDAB vesicles, whereas the use of phospholipid liposomes prepared from 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) produced an excess of the S-enantiomer. Considering the chemical structures of the reaction substrates and amphiphiles as well as the membrane structures and properties of DDAB vesicles and DOPC liposomes, it is suggested that the enantiomeric excesses result from the location of the quaternary amine of the amphiphiles and the DMGBE at the outer surface of the membrane. We show that the enantioselective reaction at the surface of the self-assembly could be regulated by adjusting the chemical structures and resulting membrane properties of the self-assembly.

Original languageEnglish
Pages (from-to)1447-1453
Number of pages7
JournalACS Omega
Volume2
Issue number4
DOIs
Publication statusPublished - 2017 Apr 30
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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