Highly Stereoselective Intermolecular Haloetherification and Haloesterification of Allyl Amides.
Highly Stereoselective Intermolecular Haloetherification and Haloesterification of Allyl Amides.
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DOI：
10.1002/anie.201502341
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发表时间：
2015-08-10
期刊：
影响因子：
--
通讯作者：
Borhan B
中科院分区：
文献类型：
--
作者：
Soltanzadeh B;Jaganathan A;Staples RJ;Borhan B
报道了烯丙基酰胺的有机催化和高区域、非对映及对映体选择性的分子间卤化醚化和卤酯化反应。各种烯烃取代基和取代模式与这种化学相容。值得注意的是，电子无偏压的烯烃底物对于标题转换表现出精致的区域和非对映选择性。我们还证明了相同的催化体系可以用于烯丙基酰胺与各种亲核试剂的氯化和溴化反应，只需很少的修饰或不进行修饰。
An organocatalytic and highly regio-, diastereo-, and enantioselective intermolecular haloetherification and haloesterification reaction of allyl amides is reported. A variety of alkene substituents and substitution patterns are compatible with this chemistry. Notably, electronically unbiased alkene substrates exhibit exquisite regio- and diastereoselectivity for the title transformation. We also demonstrate that the same catalytic system can be used in both chlorination and bromination reactions of allyl amides with a variety of nucleophiles with little or no modification.