Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 30, Pages 10700-10707Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja504532d
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Funding
- Binghamton University from the SUNY Research Foundation
- National Science Foundation through XSEDE
- NIH NIGMS [R01 GM102611, R01 GM094478]
- Ely Lilly Grantee Award
- NSF
- NDSEG
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0953259] Funding Source: National Science Foundation
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Experimental C-13 kinetic isotope effects have been used to interrogate the rate-limiting step of the Michael addition of glycinate imines to benzyl acrylate catalyzed by a chiral 2,3-bis(dicyclohexylamino) cyclopropenimine catalyst. The reaction is found to proceed via rate-limiting carbon-carbon bond formation. The origins of enantioselectivity and a key noncovalent CH center dot center dot center dot O interaction responsible for transition state organization are identified on the basis of density functional theory calculations and probed using experimental labeling studies. The resulting high-resolution experimental picture of the enantioselectivity-determining transition state is expected to guide new catalyst design and reaction development.
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