Journal
CHEMICAL SCIENCE
Volume 6, Issue 2, Pages 1537-1547Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4sc02402h
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Funding
- National Science Foundation [CHE-0953259]
- American Chemical Society Petroleum Research Fund [49279-DNI]
- NIHGMS [R01 GM102611]
- NDSEG
- NSF
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0953259] Funding Source: National Science Foundation
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We recently demonstrated that chiral cyclopropenimines are viable Bronsted base catalysts in enantioselective Michael and Mannich reactions. Herein, we describe a series of structure-activity relationship studies that provide an enhanced understanding of the effectiveness of certain cyclopropenimines as enantioselective Bronsted base catalysts. These studies underscore the crucial importance of dicyclohexylamino substituents in mediating both reaction rate and enantioselectivity. In addition, an unusual catalyst CH...O interaction, which provides both ground state and transition state organization, is discussed. Cyclopropenimine stability studies have led to the identification of new catalysts with greatly improved stability. Finally, additional demonstrations of substrate scope and current limitations are provided herein.
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