• 主题
高级搜索  >
历史搜索 清空历史
首页> 外文期刊>Chemistry: A European journal >Enantioselective vicinal bis-acylation of olefins
【24h】

Enantioselective vicinal bis-acylation of olefins

机译：烯烃的对映选择性邻位双酰化

获取原文
获取原文并翻译 | 示例
           
页面导航
  • 摘要
  • 著录项
  • 相似文献
  • 相关主题

摘要

A two-step sequence for the asymmetric vicinal acylation of olefins by a [2+2+1] strategy is reported. The key reaction is a [2+2] cycloaddition of an olefin to a chiral keteniminium salt derived from N-tosylsarcosinamide. This is followed by a regioselective Baeyer-Villiger oxidation of the resulting cyclobutanone to yield a lactol derivative that is equivalent to the product of addition of a carboxyl and a carbonyl group to the olefin. N-Tosylsarcosinamides derived from prolinol methyl ether and 2,5-dimethylpyrrolidine gave the best yields and diastereoselectivities. Five- and six-membered cycloolefins only gave cis products as expected. With seven - and eight-membered rings and cis 1,2-disubstituted acyclic olefins, partial or complete epimerisation of the cis to the trans adducts was observed. Facial selectivities were generally good except for terminal olefins. The oxidation step proceeded in high yields to give crystalline compounds which could usually be obtained in enantiopure form by simple recrystallisation.
机译：报道了通过[2 + 2 + 1]策略的烯烃不对称邻位酰化的两步序列。关键反应是烯烃与衍生自N-甲苯磺酰基肌氨酸酰胺的手性酮亚胺盐的[2 + 2]环加成反应。随后是所得环丁酮的区域选择性的Baeyer-Villiger氧化，得到的乳糖醇衍生物相当于在烯烃上加成羧基和羰基的产物。由脯氨醇甲基醚和2,5-二甲基吡咯烷衍生的N-甲苯磺酰基肌氨酸酰胺具有最佳的收率和非对映选择性。五元和六元环烯烃仅产生预期的顺式产物。用七元和八元环和顺式1，2-二取代的无环烯烃，观察到顺式部分或完全差向异构体向反式加合物的异构化。除末端烯烃外，表面选择性总体上良好。氧化步骤以高收率进行，得到结晶化合物，其通常可以通过简单的重结晶以对映纯形式获得。

著录项

相似文献

  • 外文文献
  • 中文文献
  • 专利
获取原文

客服邮箱：kefu@zhangqiaokeyan.com

京公网安备：11010802029741号 ICP备案号：京ICP备15016152号-6 六维联合信息科技 (北京) 有限公司©版权所有

  • 客服微信

  • 服务号