Elucidation of the Structures of Asymmetric Autocatalyst Based on X-ray Crystallography

作者：Matsumoto Arimasa; Fujiwara Satoshi; Abe Takaaki; Hara Atsushi; Tobita Takayuki; Sasagawa Taisuke; Kawasaki Tsuneomi; Soai Kenso

来源：Bulletin of the Chemical Society of Japan, 2016, 89(10): 1170-1177.

DOI：10.1246/bcsj.20160160

Much interest has been paid to the origin of homochirality, such as that of L-amino acids. The proposed origins of chirality have usually induced only low enantiomeric excess. Thus, asymmetric amplification by asymmetric autocatalysis has been invoked. Asymmetric autocatalysis of 5-pyrimidyl alkanol in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde is a unique example of amplification of chirality. Crystallization of possible intermediates, specifically zinc alkoxides of this 5-pyrimidyl alkanol, was investigated to obtain mechanistic insights into this reaction. Single-crystal X-ray crystallography of the formed zinc alkoxide crystals shows the existence of tetramer or higher oligomer structures in this asymmetric autocatalytic system.

• 出版日期2016-10-15