Enantioselective synthesis of near enantiopure compound by asymmetric autocatalysis triggered by asymmetric photolysis with circularly polarized light
Enantioselective synthesis of near enantiopure compound by asymmetric autocatalysis triggered by asymmetric photolysis with circularly polarized light
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DOI：
10.1021/ja0422108
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发表时间：
2005-03-16
影响因子：
15
通讯作者：
Soai, K
中科院分区：
文献类型：
--
作者：
Kawasaki, T;Sato, M;Soai, K
右旋和左旋圆偏振光（CPL）被认为是生物分子同手性的来源之一。然而，由CPL诱导的对映体过量仅非常低（<2%ee）。我们发现了由手性物理因素直接触发的不对称自催化的前所未有的例子，即右手和左手CPL，导致近对映体纯的化合物。外消旋嘧啶烷醇经r-CPL光催化不对称光解后，再经不对称自催化，可得到ee>99.5%的（R）-嘧啶烷醇，而经l-CPL光催化可得到ee>99.5%的（S）-嘧啶烷醇.
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 byr-CPL irradiation followed by asymmetric autocatalysis affords (R)-pyrimidyl alkanol with >99.5% ee. On the other hand, irradiation withl-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.