Preference of 4-exo ring closure in copper-catalyzed intramolecular coupling of vinyl bromides with alcohols
其他题名铜催化下分子内烯基溴与醇偶联反应中4-exo环合的优先
Fang YW(方烨汶); Li CZ(李超忠)
2007
发表期刊J. Am. Chem. Soc.
ISSN0002-7863
卷号129期号:26页码:8092-8093
摘要The copper-catalyzed intramolecular O-vinylation of gamma-bromohomoallylic alcohols was investigated. With 10 mol % of CuI as the catalyst and 20 mol % of 1,10-phenanthroline as the ligand, the reactions of 3-bromo-3-buten-1-ols in refluxing CH3CN led to the convenient formation of the corresponding 2-methyleneoxetanes in good to excellent yields via a 4-exo ring closure. The configuration of the CC bond was nicely retained. This methodology was then successfully extended to the cyclization in 5-exo, 6-exo, and even 6-endo modes. Moreover, the competition experiments revealed that 4-exo cyclization is fundamentally preferred over other modes of cyclization. On the other hand, the corresponding Pd(0)-catalyzed O-vinylation showed the predominance of 5-exo over 4-exo cyclization.
学科领域金属有机化学
部门归属上海有机化学研究所
URL查看原文
收录类别SCI
语种英语
WOS记录号WOS:000247563700021
引用统计
被引频次:48[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/22828
专题中科院天然产物有机化学重点实验室
通讯作者Li CZ(李超忠)
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Fang YW,Li CZ. Preference of 4-exo ring closure in copper-catalyzed intramolecular coupling of vinyl bromides with alcohols[J]. J. Am. Chem. Soc.,2007,129(26):8092-8093.
APA 方烨汶,&李超忠.(2007).Preference of 4-exo ring closure in copper-catalyzed intramolecular coupling of vinyl bromides with alcohols.J. Am. Chem. Soc.,129(26),8092-8093.
MLA 方烨汶,et al."Preference of 4-exo ring closure in copper-catalyzed intramolecular coupling of vinyl bromides with alcohols".J. Am. Chem. Soc. 129.26(2007):8092-8093.
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