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Catalytic, Enantioselective Synthesis of 1,2‐ anti ‐Diols by Asymmetric Ring‐Opening/Cross‐Metathesis
Author(s) -
Hartung John,
Grubbs Robert H.
Publication year - 2014
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.201310767
Subject(s) - enantioselective synthesis , metathesis , ruthenium , stereochemistry , catalysis , ring (chemistry) , chemistry , diol , olefin metathesis , total synthesis , salt metathesis reaction , combinatorial chemistry , organic chemistry , polymerization , polymer
An enantioselective method for the synthesis of 1,2‐ anti ‐diols has been developed. A cyclometalated chiral‐at‐ruthenium complex catalyzes the asymmetric ring‐opening/cross‐metathesis of dioxygenated cyclobutenes, thus resulting in functionally rich synthetic building blocks. Syntheses of the insect pheromone (+)‐ endo ‐brevicomin and monosaccharide ribose demonstrate the synthetic utility of the 1,2‐ anti ‐diol fragments generated in the title reaction.