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Tandem Z ‐Selective Cross‐Metathesis/Dihydroxylation: Synthesis of anti ‐1,2‐Diols
Author(s) -
Dornan Peter K.,
Wickens Zachary K.,
Grubbs Robert H.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201501505
Subject(s) - dihydroxylation , chemistry , metathesis , catalysis , tandem , stereospecificity , combinatorial chemistry , stereoselectivity , stereochemistry , homogeneous catalysis , organic chemistry , enantioselective synthesis , polymerization , polymer , materials science , composite material
A stereoselective synthesis of anti ‐1,2‐diols has been developed using a multitasking Ru catalyst in an assisted tandem catalysis protocol. A cyclometalated Ru complex catalyzes first a Z ‐selective cross‐metathesis of two terminal olefins, followed by a stereospecific dihydroxylation. Both steps are catalyzed by Ru, as the Ru complex is converted to a dihydroxylation catalyst upon addition of NaIO 4 . A variety of olefins were transformed into valuable, highly functionalized, and stereodefined molecules. Mechanistic experiments were performed to probe the nature of the oxidation step and catalyst inhibition pathways. These experiments point the way to more broadly applicable tandem catalytic transformations.