期刊
CHEMICAL SCIENCE
卷 12, 期 41, 页码 13737-13743出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc04558j
关键词
-
资金
- National Natural Science Foundation of China [22072035, 21773051, 21801056, 21901056]
- Zhejiang Provincial Natural Science Foundation of China [LZ18B020001, LQ19B040001]
Catalytic asymmetric variants for functional group transformations based on carbon-carbon bond activation are still challenging to achieve. Here, a palladium-catalyzed (3 + 2) spiro-annulation process is presented, merging C(sp(2))-C(sp(2)) sigma bond activation and click desymmetrization to form synthetically versatile oxaspiro products. The operationally straightforward and enantioselective process uses a bulky P-ligand to control enantioselective spiro-annulation, converting cyclopropenones and cyclic 1,3-diketones into chiral oxaspiro cyclopentenone-lactone scaffolds.
Catalytic asymmetric variants for functional group transformations based on carbon-carbon bond activation still remain elusive. Herein we present an unprecedented palladium-catalyzed (3 + 2) spiro-annulation merging C(sp(2))-C(sp(2)) sigma bond activation and click desymmetrization to form synthetically versatile and value-added oxaspiro products. The operationally straightforward and enantioselective palladium-catalyzed atom-economic annulation process exploits a TADDOL-derived bulky P-ligand bearing a large cavity to control enantioselective spiro-annulation that converts cyclopropenones and cyclic 1,3-diketones into chiral oxaspiro cyclopentenone-lactone scaffolds with good diastereo- and enantio-selectivity. The click-like reaction is a successful methodology with a facile construction of two vicinal carbon quaternary stereocenters and can be used to deliver additional stereocenters during late-state functionalization for the synthesis of highly functionalized or more complex molecules.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据