不斉自己触媒反応によるキラル化合物の不斉自己増殖

概要

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Asymmetric automultiplication of chiral compounds by asymmetric autocatalysis is realized for the first time where a chiral product acts as a chiral catalyst for its own production. Practically perfect asymmetric autocatalysis (>99%, >99.5% ee) is attained using pyrimidyl alkanol as an asymmetric autocatalyst in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbalde-hyde. Moreover, asymmetric autocatalyst with very low ee enhances its ee significantly up to >99.5% ee during the automultiplication without the assistance of any other chiral auxiliaries. Amino acids and [6] helicene with very low ee which are produced by asymmtric photolysis and photosynthesis using circularly polarized light (CPL) serve as chiral initiators of asymmetric auto-catalysis, and pyrimidyl alkanol with high ee is obtained. Inorganic chiral crystals such as quartz and sodium chlorate also work as chiral initiators. These results correlate for the first time the proposed origins of chirality of organic compounds such as CPL and quartz with the chirality of organic compounds with very high ee.
社団法人有機合成化学協会の論文
2002-07-01