期刊
JACS AU
卷 2, 期 5, 页码 1071-1077出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacsau.2c00186
关键词
cycloisomerization; N-acyl sulfonamides; N-sulfonyl imidates; cobalt catalysis; diverted Mukaiyama hydration
资金
- European Research Council [833540]
- Deutsche Forschungsgemeinschaft (DFG)
- European Research Council (ERC) [833540] Funding Source: European Research Council (ERC)
The cycloisomerization of beta-, gamma-, and delta-unsaturated N-acyl sulfonamides to N-sulfonyl lactams and imidates using a CoIII(salen) catalyst with t-BuOOH or air as the oxidant is reported in this study. The method exhibits good functional group tolerance and provides a new class of cyclic building blocks. The strong solvent dependence of the transformation and the synthetic versatility of the N-sulfonyl imidate product class are highlighted.
The cycloisomerization of beta-, gamma-, and delta-unsaturated N-acyl sulfonamides to N-sulfonyl lactams and imidates is reported. This transformation is effected in the presence of a CoIII(salen) catalyst using t-BuOOH or air as the oxidant. The method shows good functional group tolerance (alkyl, aryl, heteroaryl, ether, N-Boc) and furnishes an underexplored class of cyclic building blocks. The strong solvent dependence of the transformation is investigated, and the synthetic versatility of the N-sulfonyl imidate product class is highlighted.
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