Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 7, Pages 2150-2153Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b13387
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- National Science Foundation [CHE-1362498]
- University of Florida
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1362498] Funding Source: National Science Foundation
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The Cu-catalyzed synthesis of nonracemic 3-amino skipped diynes via an enantiodetermining C-C bond formation is described using StackPhos as ligand. Despite challenging issues of reactivity and stereo selectivity inherent to these chiral skipped diynes, the reaction tolerates an extremely broad substrate scope with respect to all components and provides the title compounds in excellent enantiomeric excess. The alkyne moieties are demonstrated here to be useful synthetic handles, and 3-amino skipped diynes are convenient building blocks for enantioselective synthesis.
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