Journal
ACS CATALYSIS
Volume 9, Issue 6, Pages 5184-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b01041
Keywords
stereospecific; cascade reaction; nitrogen heterocycles; solvent-controlled selectivity; allenic amide
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Funding
- Swedish Research Council [2016-03897]
- Foundation Olle Engkvist Byggmastare
- Knut and Alice Wallenberg Foundation [KAW 2016.0072]
- Vinnova [2016-03897] Funding Source: Vinnova
- Swedish Research Council [2016-03897] Funding Source: Swedish Research Council
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A palladium-catalyzed oxidative cascade reaction of alpha-tosylamide allenes has been developed. The reactivity of the allenes is controlled by the tosylamide group. In the presence of terminal alkynes the reaction proceeds via a pathway leading to a one-pot construction of pyrrole rings. Moreover, a solvent-controlled chemoselectivity of the cascade reaction was realized, leading to a stereospecific and divergent synthesis of (Z)-tetrasubstituted olefins, 2,5-dihydropyrroles, and pyrroles. Enantioenriched (Z)-tetrasubstituted olefins and 2,5-dihydropyrroles are readily synthesized by chirality transfer using this approach.
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