The Origins of Homochirality Examined by Using Asymmetric Autocatalysis

被引：65
作者：
Soai, Kenso [1 ,2 ]
Kawasaki, Tsuneomi [2 ,3 ]
Matsumoto, Arimasa [1 ]
机构：
[1] Tokyo Univ Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan
[2] Tokyo Univ Sci, Res Inst Sci & Technol, Shinjuku Ku, Tokyo 1628601, Japan
[3] Univ Fukui, Dept Mat Sci & Engn, Bunkyo Ku, Fukui 9108507, Japan
来源：
CHEMICAL RECORD | 2014年 / 14卷 / 01期
基金：
日本学术振兴会;
关键词：
autocatalysis; asymmetric amplification; asymmetric catalysis; chirality; origin of homochirality; HIGHLY ENANTIOSELECTIVE SYNTHESIS; CHIRAL-SYMMETRY-BREAKING; ENANTIOMERIC EXCESS; AMINO-ACIDS; SOAI REACTION; CRYSTAL CHIRALITY; SODIUM-CHLORATE; ZINC ALKOXIDE; AMPLIFICATION; CONJUNCTION;
D O I：
10.1002/tcr.201300028
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Pyrimidyl alkanol was found to act as an asymmetric autocatalyst in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde. Asymmetric autocatalysis of 2-alkynylpyrimidyl alkanol with an extremely low enantiomeric excess (ca. 0.00005% ee) exhibits enormous asymmetric amplification to afford the same compound with >99.5% ee. This asymmetric autocatalysis with amplification of ee has been employed to examine the validity of proposed theories of the origins of homochirality. Circularly polarized light, quartz, sodium chlorate, cinnabar, chiral organic crystals and spontaneous absolute asymmetric synthesis were considered as possible candidates for the origin of chirality; each could act as a chiral source in asymmetric autocatalysis. Asymmetric autocatalysis can discriminate the isotope chirality arising from the small difference between carbon (carbon-13/carbon-12) and hydrogen (D/H) isotopes. Cryptochiral compounds were also discriminated by asymmetric autocatalysis.
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收藏
页码：70 / 83
页数：14
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