Kinetic Resolution via Rh-Catalyzed C–C Activation of Cyclobutanones at Room Temperature | Zendy

Lin Deng | Zendy; Yue Fu | Zendy; Siu Yin Lee | Zendy; Chengpeng Wang | Zendy; Peng Liu | Zendy; Guangbin Dong | Zendy

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Kinetic Resolution via Rh-Catalyzed C–C Activation of Cyclobutanones at Room Temperature

Author(s) -

Lin Deng,

Yue Fu,

Siu Yin Lee,

Chengpeng Wang,

Peng Liu,

Guangbin Dong

Publication year - 2019

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.9b09344

Subject(s) - chemistry , catalysis , kinetic energy , rhodium , stereochemistry , photochemistry , organic chemistry , physics , quantum mechanics

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.

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