镍催化的偕立体选择性开环反应：氧杂和氮杂双环烯烃与二烷基锌试剂的反应。
Nickel-catalyzed syn-stereocontrolled ring-opening of oxa- and azabicyclic alkenes with dialkylzinc reagents.
机构信息
Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China.
出版信息
Org Biomol Chem. 2019 Jan 16;17(3):703-711. doi: 10.1039/c8ob02864h.
A new nickel-catalyzed syn-stereocontrolled ring-opening of oxa- and azabicyclic alkenes with dialkylzinc reagents was developed, which afforded the corresponding cis-2-alkyl-1,2-dihydronaphthalen-1-ols and 1,2-alkyl amide derivatives in moderate to excellent yields (up to 99% yield) under mild conditions. In this work, we successfully avoided obtaining hydride addition byproducts arising from β-hydride elimination on an ethyl nickel species. Furthermore, a plausible mechanism for the ring-opening reaction was also proposed.
一种新的镍催化的偕立体控制的氧杂和氮杂双环烯烃与二烷基锌试剂的开环反应被开发出来，在温和条件下，以中等至优秀的收率（高达 99%的收率）得到相应的顺式-2-烷基-1,2-二氢萘-1-醇和 1,2-烷基酰胺衍生物。在这项工作中，我们成功地避免了由于乙基镍物种上的β-氢消除而产生的氢化物加成副产物。此外，还提出了开环反应的合理机理。
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