Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 70, Issue 23, Pages 9538-9544Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo051651m
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Funding
- NIGMS NIH HHS [R01-GM59417] Funding Source: Medline
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The rhodium-catalyzed reaction between bis(catecholato)diboron and simple alkenes results in the syn addition of the diboron across the alkene. The resulting 1,2-bis(boronate) is subsequently oxidized to provide the 1,2-diol. In the presence of enantiomerically enriched Quinap ligand, high enantioselection in the diboration can be achieved. The reaction is highly selective for trans- and trisubstituted alkenes and can be selective for some monosubstituted alkenes as well. The development of this reaction is described as is the substrate scope and experiments that are informative about the reaction mechanism and competing pathways.
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