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Regiodivergent Addition of Phenols to Allylic Oxides: Control of 1,2‐ and 1,4‐Additions for Cyclitol Synthesis
Author(s) -
Moschitto Matthew J.,
Vaccarello David N.,
Lewis Chad A.
Publication year - 2015
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.201410228
Subject(s) - allylic rearrangement , cyclitol , palladium , phenols , chemistry , organic chemistry , medicinal chemistry , catalysis , receptor , biochemistry , inositol
Control of 1,2‐ and 1,4‐addition of substituted phenols to allylic oxides is achieved by intercepting palladium π‐allyl complexes. The interconversion of palladium complexes results in the total synthesis of MK 7607, cyathiformine B type, streptol, and a new cyclitol.