Triphenylmethyl group as a highly diastereoselective exo,endo-auxiliary in double Diels–Alder reactions with 2H-pyran-2-onesKrivec, Marko (Avtor) Štirn, Žiga (Avtor) Kočevar, Marijan (Avtor) Kranjc, Krištof (Avtor) cycloadditionsteric hindrancemicrowave chemistrybicyclo[2.2.2]octenesdiastereoselectivityThe influence of steric hindrance caused by the dienophiles on the stereoselectivity of cycloadditions of 2H-pyran-2-ones with maleimides was investigated in this study. It was found that sufficiently bulky N-substituents on the maleimides (such as N-triphenylmethyl) can cause the cycloaddition to proceed differently than expected, thus yielding asymmetric exo,endo-bicyclo[2.2.2]octenes instead of the commonly obtained symmetric exo,exo products. Furthermore, the incorporation of an N-triphenylmethyl group, which induces highly diastereoselective formation of asymmetric exo,endo adducts and can later be easily removed under acidic conditions, can be described as an example of an efficient exo,endo-diastereoselective auxiliary. 20262026-04-20 13:44:35Članek v reviji181944UDK: 547.81ISSN pri članku: 1420-3049DOI: 10.3390/molecules31081301COBISS_ID: 275826691sl