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Synfacts 2008(4): 0424-0424  
DOI: 10.1055/s-2008-1042836
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Iodine-Substituted Phosphoric Acid Catalyst

Contributor(s): Benjamin List, Frank Lay
T. Akiyama*, Y. Honma, J. Itoh, K. Fuchibe
Gakushuin University, Tokyo, Japan
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Publikationsverlauf

Publikationsdatum:
19. März 2008 (online)

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Significance

A novel chiral phosphoric acid 1 (I2-TRIP) substituted with iodine on the 6,6′-positions of the binaphthyl group is introduced. The Brønsted acid 1 catalyzes a vinylogous Mannich-type reaction of 2-trimethylsiloxyfuran (2) with aliphatic as well as aromatic and hetaromatic ald­imines 3 to give γ-butenolide derivatives 4. Interestingly, slightly higher enantioselectivity was achieved with the iodine-substituted phosphoric acid 1 (I2-TRIP, er = 91:9) compared to the non-iodine-substituted phosphoric acid (TRIP, er = 87:13), retaining the same high yield (100% yield with both catalysts).