Journal
ORGANIC LETTERS
Volume 22, Issue 4, Pages 1355-1359Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b04584
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- Welch Foundation [E-1744]
- NSF [CHE-1800499]
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Organocatalysis was shown to facilitate conjugate additions to vinylogous esters and amides for the first time. Subsequent elimination of a beta-alcohol or amine provided pi-conjugated beta-substituted enones. Remarkably, nucleophile addition to the electron-rich vinylogous substrates is more rapid than classical enones, forming monosubstituted products. A doubly organocatalytic (organic diol and methyl aniline) conjugate addition synthesized the products directly from alkynyl ketones. Both of these catalytic transformations are orthogonal to transition metal catalysis, allowing for good yields, easily accessible or commercially available reagents, high selectivity, reagent recovery and recyclability, facile scalability, and exceptional functional group tolerance.
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