Kinetic Resolution via Rh-Catalyzed C-C Activation of Cyclobutanones at Room Temperature
Kinetic Resolution via Rh-Catalyzed C-C Activation of Cyclobutanones at Room Temperature
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DOI：
10.1021/jacs.9b09344
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发表时间：
2019-10-16
影响因子：
15
通讯作者：
Dong, Guangbin
中科院分区：
文献类型：
--
作者：
Deng, Lin;Fu, Yue;Dong, Guangbin
Herein we describe the development of a highly selective kinetic resolution of cyclobutanones via a Rh-catalyzed "cut-and-sew" reaction with selectivity factor up to 785. This reaction takes place at room temperature with excellent efficiency. Various trans-5,6-fused bicycles and C2-substituted cyclobutanones were obtained with excellent ee's that can be further used as chiral building blocks. DFT calculations reveal the crucial roles of the DTBM-segphos ligand in stabilizing the rate- and enantioselectivity-determining C-C oxidative addition transition state via favorable ligand substrate dispersion interactions.
