Addition of Cl2C: to (-)-O-menthyl acrylate under sonication-phase-transfer catalysis. Efficient synthesis of (+)- and (-)-(2-chlorocyclopropyl)methanol.
Addition of Cl2C: to (-)-O-menthyl acrylate under sonication-phase-transfer catalysis. Efficient synthesis of (+)- and (-)-(2-chlorocyclopropyl)methanol.
复制标题
在超声相转移催化下将 Cl2C 加成到 (-)-O-丙烯酸薄荷酯上。
DOI：
10.1021/jo0480186
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发表时间：
2005
期刊：
影响因子：
--
通讯作者：
Molinski,TadeuszF
中科院分区：
文献类型：
--
作者：
Masuno,MakotoN;Young,DouglasM;Hoepker,AlexanderC;Skepper,ColinK;Molinski,TadeuszF
Dichlorocyclopropanation of (−)-O-menthyl acrylate under conditions of phase-transfer catalysis (CHCl3, KOH, tetramethylammonium bromide), with sonication, gives excellent yields (85−94%) of the corresponding dichlorocyclopropanecarboxylate ester compared to thermal conditions (90 °C, 56%). No diastereoselectivity was observed, but one isomer was isolated pure by fractional crystallization. The measured kinetic isotope effect (initial rate (CHCl3)/rate (CDCl3) ∼1.7) suggests deprotonation of CHCl3as the rate-limiting step.
