Efficient Intramolecular Cyclizations of Phenoxyethynyl Diols into Multisubstituted α,β-Unsaturated Lactones
Efficient Intramolecular Cyclizations of Phenoxyethynyl Diols into Multisubstituted α,β-Unsaturated Lactones
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DOI：
10.1021/ol401824v
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发表时间：
2013-08-16
期刊：
影响因子：
5.2
通讯作者：
Akai, Shuji
中科院分区：
文献类型：
--
作者：
Egi, Masahiro;Ota, Yuya;Akai, Shuji
AgOTf催化的苯氧基乙炔基二醇的分子内环化在温和条件下进行，以55-98%的产率得到多取代的α，β-不饱和-γ-内酯。该方法也适用于α，β-不饱和-δ-内酯的合成。当用化学计量的N-溴代琥珀酰亚胺代替AgOTf时，进行类似的环化，得到α-溴取代的α，β-不饱和内酯。
AgOTf-catalyzed intramolecular cyclization of phenoxyethynyl diols proceeded under mild conditions to afford the multisubstituted alpha,beta-unsaturated-gamma-lactones in 55-98% yields. This method was also applicable to the synthesis of alpha,beta-unsaturated-delta-lactones. A similar cyclization proceeded when AgOTf was replaced with a stoichiometric amount of N-bromosuccinimide to furnish the a-bromo-substituted alpha,beta-unsaturated lactones.