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Iridium‐Catalyzed Intermolecular Allylic Etherification with Aliphatic Alkoxides: Asymmetric Synthesis of Dihydropyrans and Dihydrofurans
Author(s) -
Shu Chutian,
Hartwig John F.
Publication year - 2004
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200460214
Subject(s) - allylic rearrangement , stereocenter , phosphoramidite , iridium , catalysis , chemistry , intermolecular force , organic chemistry , enantioselective synthesis , molecule , dna , biochemistry , oligonucleotide
Hindered chiral ethers with one or two stereocenters are now readily available by allylic etherification of primary and secondary alkoxides (see reaction). When an Ir–phosphoramidite complex is used as the catalyst, the reaction proceeds with high regio‐, enantio‐, and diastereoselectivity. Np=1‐naphthyl.