Zhao Ming, Chen Jie, Yang Hui, Zhou Ling
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry and Materials Science, Northwest University, Xi'an, 710127, P. R. China.
Chemistry. 2017 Feb 24;23(12):2783-2787. doi: 10.1002/chem.201700198. Epub 2017 Feb 3.
An efficient enantioselective N-heterocyclic carbene (NHC)-catalyzed intramolecular S 2' nucleophilic substitution of aldehydes with (E/Z)-trisubstituted allylic bromides was accomplished. A range of enantioenriched chromanones bearing an all-carbon quaternary stereocenter at the C3 position were prepared with up to 97 % yield and 98 % enantiomeric excess. The resulting vinyl and carbonyl groups in these products can be transformed into a variety of synthetically important building blocks.
实现了一种高效的对映选择性N-杂环卡宾（NHC）催化的醛与（E/Z）-三取代烯丙基溴的分子内S 2'亲核取代反应。制备了一系列在C3位置带有全碳季立体中心的对映体富集色满酮，产率高达97%，对映体过量高达98%。这些产物中生成的乙烯基和羰基可转化为各种具有重要合成意义的结构单元。
