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Chiral Anion Catalysis in the Enantioselective 1,4‐Reduction of the 1‐Benzopyrylium Ion as a Reactive Intermediate
Author(s) -
Terada Masahiro,
Yamanaka Takuto,
Toda Yasunori
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201302486
Subject(s) - enantioselective synthesis , ion , reduction (mathematics) , catalysis , chemistry , combinatorial chemistry , reactive intermediate , organic chemistry , mathematics , geometry
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 2 H ‐chromen‐2‐ol derivatives to generate the achiral 1‐benzopyrylium ion as a reactive key intermediate.