Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 41, Pages 16260-16265Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b09344
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Funding
- NIGMS [2R01GM109054]
- NSF [CHE-1654122]
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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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