Asymmetric Synthesis by Using Natural Sunlight under Absolute Achiral Conditions

Masami Sakamoto; Koh Shiratsuki; Naohiro Uemura; Hiroki Ishikawa; Yasushi Yoshida; Yoshio Kasashima; Takashi Mino

doi:10.1002/chem.201605583

Asymmetric Synthesis by Using Natural Sunlight under Absolute Achiral Conditions

Chemistry. 2017 Jan 31;23(7):1717-1721. doi: 10.1002/chem.201605583. Epub 2017 Jan 4.

Authors

Masami Sakamoto¹, Koh Shiratsuki¹, Naohiro Uemura¹, Hiroki Ishikawa¹, Yasushi Yoshida¹, Yoshio Kasashima², Takashi Mino¹

Affiliations

¹ Department of Applied Chemistry and Biotechnology, Graduate School of Engineering and Molecular Chirality Research Center, Chiba University, Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan.
² Education Center, Faculty of Engineering, Chiba Institute of Technology, Shibazono, Narashino, Chiba, 275-0023, Japan.

PMID: 27910157
DOI: 10.1002/chem.201605583

Abstract

Irradiation of prochiral (E)-aroylacrylamide with sunlight gave single-handed pyrrolinone quantitatively and with an enantiomeric excess (ee) of over 99 % under absolutely achiral conditions. The phenomenon was explained by photoisomerization and reversible cyclization followed by dynamic crystallization involving deracemization.

Keywords: asymmetric synthesis; chiral amplification; deracemization; dynamic crystallization; photoisomerization.