Enantioselective synthesis of near enantiopure compound by asymmetric autocatalysis triggered by asymmetric photolysis with circularly polarized light

Tsuneomi Kawasaki, Mirai Sato, Saori Ishiguro, Takahiro Saito, Yosuke Morishita, Itaru Sato, Hideo Nishino, Yoshihisa Inoue, Kenso Soai

Research output: Contribution to journalArticlepeer-review

173 Citations (Scopus)

Abstract

Right- and left-handed circularly polarized light (CPL) has been proposed as one of the origins of homochirality of biomolecules. However, the enantiomeric excess induced by CPL has been only very low (<2% ee). We found the unprecedented example of asymmetric autocatalysis triggered directly by a chiral physical factor, that is, right- and left-handed CPL, leading to a near enantiopure compound. Asymmetric photolysis of racemic pyrimidyl alkanol by r-CPL irradiation followed by asymmetric autocatalysis affords (R)-pyrimidyl alkanol with >99.5% ee. On the other hand, irradiation with l-CPL affords (S)-pyrimidyl alkanol with >99.5% ee. Thus, chiral physical power, such as CPL, in conjunction with asymmetric autocatalysis, provides a highly enantioenriched compound.

Original languageEnglish
Pages (from-to)3274-3275
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number10
DOIs
Publication statusPublished - 2005 Mar 16

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Enantioselective synthesis of near enantiopure compound by asymmetric autocatalysis triggered by asymmetric photolysis with circularly polarized light'. Together they form a unique fingerprint.

Cite this