Enantioselective Synthesis of Near Enantiopure Compound by Asymmetric Autocatalysis Triggered by Asymmetric Photolysis with Circularly Polarized Light

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• 作者：Tsuneomi Kawasaki ; Mirai Sato ; Saori Ishiguro ; Takahiro Saito ; Yosuke Morishita ; Itaru Sato ; Hideo Nishino ; Yoshihisa Inoue ; and Kenso Soai
• 刊名：Journal of the American Chemical Society
• 出版年：2005
• 出版时间：March 16, 2005
• 年：2005
• 卷：127
• 期：10
• 页码：3274 - 3275
• 全文大小：55K
• 年卷期：v.127,no.10(March 16, 2005)
• ISSN：1520-5126

文摘

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.