Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 14, Pages 5133-5139Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b00564
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Funding
- NIH [GM-033049]
- NSF [NSF CHE-1360634]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1360634] Funding Source: National Science Foundation
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Enamides represent bioactive pharmacophores in various natural products, and have become increasingly common reagents for asymmetric incorporation of nitrogen functionality. Yet the synthesis of the requisite geometrically defined enamides remains problematic, especially for highly substituted and Z-enamides. Herein we wish to report a general atom economic method for the isomerization of a broad range of N-allyl amides to form Z-di-, tri-, and tetrasubstituted enamides with exceptional geometric selectivity. This report represents the first examples of a catalytic isomerization of N-allyl amides to form nonpropenyl disubstituted, tri- and tetrasubstituted enamides with excellent geometric control. Applications of these geometrically defined enamides toward the synthesis of cis vicinal amino alcohols and tetrasubstituted alpha-borylamido complexes are discussed.
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