N-Heterocyclic Carbene Catalyzed Synthesis of δ-Sultones via α,β-Unsaturated Sulfonyl Azolium Intermediates.
A limited array of reactive intermediates have enabled a wealth of discoveries in N-heterocyclic carbene organocatalysis. In this study, the viability of α,β-unsaturated sulfonyl azoliums as double electrophiles in new reactions is examined. Specifically, the (3+3) annulation of such species with the trimethylsilyl enol ethers of various 1,3-dicarbonyl compounds has been developed. This reaction provides access to a range of novel unsaturated δ-sultones (18 examples) in good yields (40-88 %) under mild reaction conditions. Mechanistic studies and the development of an enantioselective variant (55 % yield, 73:27 e.r.) support the intermediacy of an α,β-unsaturated sulfonyl azolium species.
School of Chemistry, Monash University, Clayton 3800, Victoria (Australia).
Andrei
A
Ungureanu
School of Chemistry, Monash University, Clayton 3800, Victoria (Australia).
Alison
A
Levens
School of Chemistry, Monash University, Clayton 3800, Victoria (Australia).
Lisa
L
Candish
School of Chemistry, Monash University, Clayton 3800, Victoria (Australia). david.lupton@monash.edu.
David W
DW
Lupton
N-heterocyclic carbenes; nucleophilic catalysis; organocatalysis; sulfonyl azolium intermediates; sulfonyl fluorides