1488-21-7Relevant academic research and scientific papers
Synthesis and Desymmetrization of meso Tricyclic Systems Derived from Benzene Oxide
Matías, Desirée M.,Johnson, Jeffrey S.
, p. 4859 - 4866 (2018/04/26)
Ozonolysis of the Diels-Alder adducts derived from benzene oxides and N-alkylmaleimides resulted in fully substituted, meso bicyclic systems bearing six contiguous stereocenters, isolated as diols upon reductive workup with NaBH4. Variation in the workup allowed for isolation of two different diastereoisomers, through double epimerization of the imide stereocenters. Desymmetrization of the resulting meso diols via asymmetric nucleophilic epoxide opening and acylation reactions provided access to highly substituted, enantioenriched fused rings.
?-Facial stereoselectivity in the Diels-Alder reactions of benzene oxides
Gillard, James R.,Newlands, Michael J.,Bridson, John N.,Burnell, D. Jean
, p. 1337 - 1343 (2007/10/02)
The Diels-Alder reactions of N-phenylmaleimide and dimethyl acetylenedicarboxylate with benzene oxide (1,3,5-cyclohexatriene 1,2-oxide, 3) and its more substituted derivatives 1,2-dimethyl-1,3,5-cyclohexatriene 1,2-oxide (7) and 10-oxatricyclodeca-2,4-diene (11) in a kinetic manner gave exclusively products of addition anti to the plane-nonsymmetrical oxygen.The structures of the adducts were determined unequivocally by nuclear Overhauser enhancements in their 1H nuclear magnetic resonance spectra and by X-ray crystallographic methods.The ?-facial stereoselectivity was rationalized in terms of unfavorable orbital interactions, steric hindrance between the dienophile and the syn face of benzene oxide, and ?-donation by the oxygen. Key words: cycloaddition, Diels-Alder, syn-anti, ?-facial stereoselectivity, benzene oxide.
