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Transition-metal-catalyzed enantioselective synthesis and functionalization of 1,2- and 1,4-bis(boronate)esters

Posted on:2009-01-25Degree:Ph.DType:Dissertation
University:Boston CollegeCandidate:Burks, Heather ElizabethFull Text:PDF
GTID:1441390002994215Subject:Chemistry
Abstract/Summary:
The first examples of an enantioselective allene diboration and diene diboration are reported. The asymmetric palladium-catalyzed allene diboration afforded 1,2-bis(boronate)esters in up to 98% ee. The reaction development for the allene diboration, as well as the expansion of the substrate scope, and elucidation of the reaction mechanism are reported. Following the development of the enantioselective allene diboration, the first enantioselective diene diboration was disclosed. 1,4-Dihydroxylation products resulting from a tandem diene diboration/oxidation sequence are obtained in up to 92% ee.
Keywords/Search Tags:Diboration, Enantioselective, Diene
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