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Enantioselective Desymmetrization of meso ‐Decalin Diallylic Alcohols by a New Zr‐Based Sharpless AE Process: A Novel Approach to the Asymmetric Synthesis of Polyhydroxylated Celastraceae Sesquiterpene Cores
Author(s) -
Spivey Alan C.,
Woodhead Steven J.,
Weston Matthew,
Andrews Benjamin I.
Publication year - 2001
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 - 10.1002/1521-3773(20010216)40:4<769::aid-anie7690>3.0.co;2-5
Subject(s) - celastraceae , desymmetrization , enantioselective synthesis , sharpless epoxidation , sharpless asymmetric dihydroxylation , phenylacetate , chemistry , stereochemistry , sesquiterpene , organic chemistry , catalysis , biochemistry
Zirconium to the rescue! Eight contiguous chiral centers can be established with >95 % ee in the key step of an asymmetric synthetic approach to the cores of certain Celastraceae sesquiterpenes (see scheme). The route required the development of a new zirconium‐modified Sharpless asymmetric epoxidation instead of the traditional titanium version. DIPT=diisopropyl tartrate.