Premium
Asymmetric One‐Pot Sequential Organo‐ and Gold Catalysis for the Enantioselective Synthesis of Dihydropyrrole Derivatives
Author(s) -
Monge David,
Jensen Kim L.,
Franke Patrick T.,
Lykke Lennart,
Jørgensen Karl Anker
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001123
Subject(s) - hydroamination , enantioselective synthesis , bifunctional , chemistry , catalysis , isomerization , combinatorial chemistry , malononitrile , alkyne , organic chemistry , compatibility (geochemistry) , materials science , composite material
A direct asymmetric one‐pot synthesis of optically active 2,3‐dihydropyrroles from propargylated malononitrile and N ‐Boc‐protected (Boc= tert ‐butoxycarbonyl) imines is presented. The approach is based on a bifunctional organocatalytic Mannich‐type reaction and a subsequent gold‐catalyzed alkyne hydroamination and isomerization. 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 enantioselectivities (up to 88 % ee ). The absolute configuration of the final products is unambiguously established by X‐ray analysis. To highlight the synthetic potential of the accessed heterocyclic compounds, their transformation into 1‐pyrrolines, which represent direct precursors of pyrrolidines, is presented.