Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 43, Pages 17106-17109Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja203087a
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Funding
- NSF [CAREER CHE-0748525]
- NSF-CRIF [CHE-0946990]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0946990] Funding Source: National Science Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0748525] Funding Source: National Science Foundation
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Nonbiaryl axially chiral 2-pyridones were synthesized and employed for light-induced electrocyclic 4 pi ring closure leading to bicyclo-beta-lactam photoproducts in solution. The enantioselectivity in the photoproducts varied from 22 to 95% depending on the reaction temperature and the ability of the axially chiral chromophore to form intramolecular and/or intermolecular H-bonds with the solvent. On the basis of the differential activation parameters, entropic control of the enantiospecificity was observed for 2-pyridones lacking the ability to form H-bonds. Conversely, enthalpy played a significant role for 2-pyridones having the ability to form H-bonds.
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