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Design of Brønsted Acid-Assisted Chiral Lewis Acid (BLA) Catalysts for Highly Enantioselective Diels−Alder Reactions by Kazuaki Ishihara; Hideki Kurihara; Masayuki Matsumoto; Hisashi Yamamoto is a Chemistry article available to read on EtoBox.

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Brønsted acid-assisted chiral Lewis acid (BLA) was highly effective as a chiral catalyst for the enantioselective Diels-Alder reaction of both R-substituted and R-unsubstituted R,β-enals with various dienes. Hydroxy groups in optically active binaphthol derivatives and boron reagents with electron-withdrawing substituents were used as Brønsted acids and Lewis acids, respectively. Intramolecular Brønsted acids in a chiral BLA catalyst played an important role in accelerating the rate of Diels-Alder reactions and in producing a high level of enantioselectivity. In particular, excellent enantioselectivity was achieved due to intramolecular hydrogen bonding interaction and attractive π-π donor-acceptor interaction in the transition-state assembly by hydroxy aromatic groups in a chiral BLA catalyst.

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Author

Kazuaki Ishihara; Hideki Kurihara; Masayuki Matsumoto; Hisashi Yamamoto

Publisher

American Chemical Society (ACS)

Published

1998

Language

EN

Field

Chemistry (Physical Sciences)