Publication | Open Access
Palladium‐Catalyzed Asymmetric Construction of Vicinal All‐Carbon Quaternary Stereocenters and its Application to the Synthesis of Cyclotryptamine Alkaloids
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Citations
41
References
2013
Year
Chemical EngineeringCyclotryptamine AlkaloidsInitial Matched AllylationEngineeringCross-coupling ReactionOrganic ChemistryCatalysisFormal SynthesesChemistryStereoselective SynthesisPharmacologyAsymmetric CatalysisAsymmetric ConstructionEnantioselective Synthesis
A twofold Pd-DAAA Pd-catalyzed decarboxylative allylic alkylation (see scheme) was used to construct two vicinal all-carbon quaternary stereocenters (marked in red) in a diastereo- and enantioselective fashion. The products of the Pd-DAAA were further elaborated to complete the formal syntheses of cyclotryptamine alkaloids. The twofold Pd-catalyzed transformation proceeds through an initial matched allylation followed by a second mismatched allylation to deliver the desired product.
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