Enantioselective Photochemical Reactions of 2-Pyridones in Solution
- 26 January 2001
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (4) , 601-603
- https://doi.org/10.1021/ol007004t
Abstract
Two key photochemical reactions of prochiral 2-pyridones were studied in the presence of a chiral host. The [4 + 4]-photocycloaddition with cyclopentadiene (CpH) proceeded smoothly and with high enantioselectivity (84−87% ee). The absolute configuration of the endo-diastereoisomer was established by X-ray crystallography. The electrocyclic [4π]-ring closure to 3-oxo-2-azabicyclo[2.2.0]-5-hexenes occurred with lower enantioselectivity (20−23% ee at −20 °C). The velocity of the latter reaction slowed significantly with decreasing temperature.Keywords
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