jo8b01273_si_003.cif (15.1 kB)

Asymmetric Diels–Alder Reaction Involving Dynamic Enantioselective Crystallization

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posted on 28.05.2018 by Naohiro Uemura, Seiya Toyoda, Hiroki Ishikawa, Yasushi Yoshida, Takashi Mino, Yoshio Kasashima, Masami Sakamoto
Asymmetric Diels–Alder reaction was achieved under achiral conditions. Reaction of prochiral 2-methylfuran and N-phenylmaleimide in heptane or hexane solution at 80 °C efficiently gave a conglomerate crystal of exo-type Diels–Alder adduct selectively, and continuous suspension of the reaction mixture with glass beads promoted attrition-enhanced deracemization, leading to an optically active exo-adduct in 90% ee.