Novel asymmetric formylation of aromatic compounds: Enantioselective synthesis of formyl 7,8- dipropyltetrathia[7]helicenes

Julien Doulcet, G. Richard Stephenson

Research output: Contribution to journalArticle

18 Citations (Scopus)
12 Downloads (Pure)

Abstract

Asymmetric formylation of aromatic compounds is virtually unexplored. We report the synthesis and evaluation of a library including 20 new chiral formamides in the kinetic resolution of 7,8-dipropyltetrathia[7]helicene, affording the corresponding formyl- or diformylhelicenes in up to 73% ee, making enantiopure compounds available by recrystallisation. With the N,N-disubstituted formamides used in this
study, the best enantioselectivity has been achieved with R1=iPr, R2=Me, R3=H, R4=1-naphthyl or its 1-pyrenyl equivalent.
Original languageEnglish
Pages (from-to)13431–13436
Number of pages6
JournalChemistry - A European Journal
Volume21
Issue number38
Early online date4 Aug 2015
DOIs
Publication statusPublished - 14 Sep 2015

Keywords

  • asymmetric synthesis
  • chiral formamides
  • double kinetic resolution
  • enantioselective formylation
  • kinetic resolution

Cite this