Chiral Anion Catalysis in the Enantioselective 1,4-Reduction of the 1-Benzopyrylium Ion as a Reactive Intermediate

Anionic! Novel chiral anion catalysis of the enantioselective 1,4‐reduction of the 1‐benzopyrylium ion by a chiral phosphoric acid was accomplished with a Hantzsch ester as the reducing agent. The enantioselective reduction established is composed of a two‐step consecutive transformation involving s...

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Bibliographic Details
Published in:Chemistry : a European journal 2013-10, Vol.19 (41), p.13658-13662
Main Authors: Terada, Masahiro, Yamanaka, Takuto, Toda, Yasunori
Format: Article
Language:English
Subjects:
Anions
asymmetric catalysis
benzopyrylium
Brønsted acids
Catalysis
Chemistry
Derivatives
enantioselective reduction
Esters
organocatalysis
Phosphoric acid
Reducing agents
Reduction
Transformations
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Summary:Anionic! Novel chiral anion catalysis of the enantioselective 1,4‐reduction of the 1‐benzopyrylium ion by a chiral phosphoric acid was accomplished with a Hantzsch ester as the reducing agent. The enantioselective reduction established is composed of a two‐step consecutive transformation involving stereoablative loss of the hydroxy group from racemic 2H‐chromen‐2‐ol derivatives to generate the achiral 1‐benzopyrylium ion as a reactive key intermediate.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201302486