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Asymmetric Synthesis by Using Natural Sunlight under Absolute Achiral Conditions
Author(s) -
Sakamoto Masami,
Shiratsuki Koh,
Uemura Naohiro,
Ishikawa Hiroki,
Yoshida Yasushi,
Kasashima Yoshio,
Mino Takashi
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201605583
Subject(s) - photoisomerization , sunlight , absolute configuration , enantiomeric excess , irradiation , crystallization , enantiomer , absolute (philosophy) , chemistry , isomerization , enantioselective synthesis , stereochemistry , organic chemistry , optics , physics , catalysis , philosophy , nuclear physics , epistemology
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.