Asymmetric One-Pot Sequential Organo- and Gold Catalysis for the Enantioselective Synthesis of Dihydropyrrole Derivatives

Autor:	David Monge, Patrick T. Franke, Lennart Lykke, Kim L. Jensen, Karl Anker Jørgensen
Rok vydání:	2010
Předmět:	chemistry.chemical_classification Chemistry Stereochemistry Organocatalysis Organic Chemistry Enantioselective synthesis Alkyne General Chemistry Hydroamination Optically active Catalysis
Zdroj:	Monge, D, Jensen, K L, Franke, P T, Lykke, L & Jørgensen, K A 2010, ' Asymmetric One-Pot Sequential Organo-and Gold Catalysis for the Enantioselective Synthesis of Dihydropyrrole Derivatives ', Chemistry: A European Journal, vol. 16, no. 31, pp. 9478-9484 .
ISSN:	0947-6539
Popis:	A direct asymmetric one-pot synthesis of optically active 2,3-dihy- dropyrroles from propargylated malo- nonitrile and N-Boc-protected (Boc = tert-butoxycarbonyl) imines is present- ed. The approach is based on a bifunc- tional organocatalytic Mannich-type re- action and a subsequent gold-catalyzed alkyne hydroamination and isomeriza- tion. The compatibility of both catalytic systems is presented and the overall transformation results in good yields (up to 70 %) with high selectivities (endo/exo > 10:1) and enantioselectivi- ties (up to 88 % ee). The absolute con- figuration of the final products is un- ambiguously established by X-ray anal- ysis. To highlight the synthetic potential of the accessed heterocyclic com- pounds, their transformation into 1-pyr- rolines, which represent direct precur- sors of pyrrolidines, is presented.
Databáze:	OpenAIRE
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