Cobalt-Catalyzed Cyclization of Unsaturated N -Acyl Sulfonamides: a Diverted Mukaiyama Hydration Reaction
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Implication
Synthetic methodology study reveals cobalt-catalyzed cyclization of unsaturated N-acyl sulfonamides into sulfonyl lactams, highlighting new routes to versatile cyclic building blocks.
Key Points
- Develop a catalytic cyclization pathway for unsaturated N-acyl sulfonamides to access underexplored cyclic building blocks via a diverted Mukaiyama hydration strategy.
- Applied a Co(III)(salen) catalyst with tert-butyl hydroperoxide (t-BuOOH) or air as terminal oxidants across β-, γ-, and δ-unsaturated N-acyl sulfonamides.
- Evaluated functional group compatibility across diverse moieties, including alkyl, aryl, heteroaryl, ether, and N-Boc substituents.
- Investigated the impact of reaction solvents on reaction pathways and assessed the synthetic versatility of the resulting N-sulfonyl imidate scaffolds.
- Successfully converted β-, γ-, and δ-unsaturated precursors into corresponding N-sulfonyl lactams and imidates.
- Demonstrated high functional group tolerance and established that reaction selectivity is strongly solvent-dependent.
Cite This Study
Fischer et al. (2022) studied this question.