Beilstein J. Org. Chem.2016,12, 1136–1152, doi:10.3762/bjoc.12.110
asymmetric redox bicycloisomerization of 1,6- and 1,7-enynes. This complex was used to synthesize a broad array of [3.1.0] and [4.1.0] bicycles. Sulfonamide- and phosphoramidate-containing products could be deprotected under reducing conditions. Catalysis performed with enantiomerically enriched propargyl
alcohols revealed a matched/mismatched effect that was strongly dependent on the nature of the solvent.
Keywords: asymmetric catalysis; [3.1.0] bicycles; [4.1.0] bicycles; cycloisomerization; 1,6-enyne; 1,7-enyne; ruthenium catalysis; sulfoxide; Introduction
Due to their prevalence in natural products [1
asymmetric ruthenium-catalyzed cycloisomerization reactions in the literature. In 2011, our research group disclosed the ruthenium-catalyzed redox bicycloisomerization of 1,6- and 1,7-enynes to construct structurally complex [3.1.0] and [4.1.0] bicycles containing vicinal, quaternary all-carbon stereocenters
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Graphical Abstract
Scheme 1:
Divergent behavior of the palladium and ruthenium-catalyzed Alder–ene reaction.