title: Enantioselective synthesis of near enantiopure compound by asymmetric autocatalysis triggered by asymmetric photolysis with circularly polarized light.
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.
authors.affiliation: Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo, 162-8601 Japan.
authors.forename: Tsuneomi
authors.initials: T
authors.lastname: Kawasaki
authors.forename: Mirai
authors.initials: M
authors.lastname: Sato
authors.forename: Saori
authors.initials: S
authors.lastname: Ishiguro
authors.forename: Takahiro
authors.initials: T
authors.lastname: Saito
authors.forename: Yosuke
authors.initials: Y
authors.lastname: Morishita
authors.forename: Itaru
authors.initials: I
authors.lastname: Sato
authors.forename: Hideo
authors.initials: H
authors.lastname: Nishino
authors.forename: Yoshihisa
authors.initials: Y
authors.lastname: Inoue
authors.forename: Kenso
authors.initials: K
authors.lastname: Soai