An Investigation of the Diels-Alder Cycloadditions of 2(H)-1,4-Oxazin-2-ones.
Publication date
2005Keyword
Oxygen nitrogen heterocycleNitrogen heterocycle
Oxygen heterocycle
Ketone
Oxazine derivatives
Density functional method
Stereochemistry
Piperidine derivatives
Lactone
Diels Alder addition
Stereoselectivity
Regioselectivity
Peer-Reviewed
Yes
Metadata
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Forumla chem. . A variety of 5-chloro-2(H)-1,4-oxazin-2-ones bearing a range of substituents at their 3- and 6-positions undergo Diels-Alder cycloaddition as a 2-azadiene component with electron-rich, electron-deficient, and electron-neutral dienophiles. These reactions proceed with moderate regio- and stereoselectivity to afford relatively stable and readily isolable bridged bicyclic lactone cycloadducts. Chemical manipulation of these cycloadducts affords highly substituted and functionally rich piperidines. The regio- and stereochemical preferences of the cycloadditions of 5-chloro-2(H)-1,4-oxazin-2-ones are investigated computationally using density functional theory (B3LYP/6-31G*).Version
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Afarinkia, K., Bahar, A., Bearpark, M.J. and Garcia-Ramos, J et al. (2005). An Investigation of the Diels-Alder Cycloadditions of 2(H)-1,4-Oxazin-2-ones. Journal of Organic Chemistry. Vol. 70, No. 23, pp. 9529-9537.Link to Version of Record
https://doi.org/10.1021/jo051646iType
Articleae974a485f413a2113503eed53cd6c53
https://doi.org/10.1021/jo051646i