Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 16, Pages 9300-9304Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01273
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Funding
- Ministry of Education, Culture, Sports, Science, and Technology (MEXT) of the Japanese Government [25288017, 26410124, 16H04144]
- Frontier Science Program of Graduate School of Science and Engineering, Chiba University
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Asymmetric Diels-Alder reaction was achieved under achiral conditions. Reaction of prochiral 2-methylfuran and N-phenylmaleimide in heptane or hexane solution at 80 degrees 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.
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