Rhodium-Catalyzed Domino Hydroformylation/Double-Cyclization Reaction of Arylacetylenecarboxamides: Diastereoselectivity Studies and Application in the Synthesis of 1-Azabicyclo[x.y.0]alkanes.
作者： Jui-Chi Tsai , Yi-Huei Lin , Guei-Tang Chen , Yu-Kai Gao , Yu-Che Tseng
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摘要: A domino method for the rapid syntheses of 1-azabicyclo[x.y.0]alkane scaffolds, such as indolizidines, quinolizidines, decahydropyridoazepines, and their derivatives, has been developed. This strategy involved a rhodium-catalyzed hydroformylation allyl-, 3-butenyl-, or homoallyl amides, followed by two spontaneous ring closures under mild conditions. The reaction scope diastereoselectivity were fully explored changing substitution pattern on amide altering length carbon chain. was applied to natural alkaloids tashiromine epilupinine. clear differences between reactivities isomeric substrates, 3-butenamide 1 j 1 i, could be attributed better HOMO-LUMO overlap in transition states that derived from butenamides during cyclization. explanation supported DFT calculations.
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