Asymmetric automultiplication of chiral compounds by asymmetric autocatalysis

Kenso Soai*, Itaru Sato, Takanori Shibata

*この研究の対応する著者

研究成果: Article査読

15 被引用数 (Scopus)

抄録

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-carbaldehyde. Moreover, asymmetric autocatalyst with very low ee enhances its ee significantly up to > 99.5% ee during the automultiplicafion 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 autocatalysis, 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.

本文言語English
ページ(範囲)668-678
ページ数11
ジャーナルYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
60
7
DOI
出版ステータスPublished - 2002 7月
外部発表はい

ASJC Scopus subject areas

  • 有機化学

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