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Silver‐Catalyzed Asymmetric Synthesis of 2,3‐Dihydrobenzofurans: A New Chiral Synthesis of Pterocarpans
Author(s) -
JiménezGonzález Leticia,
GarcíaMuñoz Sergio,
ÁlvarezCorral Miriam,
MuñozDorado Manuel,
RodríguezGarcía Ignacio
Publication year - 2006
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.200600332
Subject(s) - enantioselective synthesis , catalysis , condensation , fluoride , chemistry , antifungal , combinatorial chemistry , organic chemistry , inorganic chemistry , physics , medicine , dermatology , thermodynamics
2,3‐Dihydrobenzofurans can be diastereoselectively prepared by condensation of aromatic aldehydes with 2,3‐dihydrobenzoxasilepines under the catalysis of Ag I complexes, and in the presence of a source of fluoride ion. The application of this strategy by using chiral catalysts leads to a new enantioselective total synthesis of natural cis ‐pterocarpans and their trans isomers. Through this method, the first enantioselective total synthesis of the antifungal agent (−)‐pterocarpin was achieved. In addition, a new entry into the heteroaromatic system of 2,5‐dihydrobenzoxepine is also presented.