20.500.12556/RUL-181944 Triphenylmethyl group as a highly diastereoselective exo,endo-auxiliary in double Diels–Alder reactions with 2H-pyran-2-ones The 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. cycloaddition steric hindrance microwave chemistry bicyclo[2.2.2]octenes diastereoselectivity cikloadicija sterična oviranost mikrovalovna kemija biciklo[2.2.2]okteni diastereoselektivnost true false true Angleški jezik Slovenski jezik Članek v reviji 2026-04-20 13:44:35 2026-04-20 13:44:36 2026-04-21 04:42:31 0000-00-00 00:00:00 2026 0 0 29 str. iss. 8, art. 1301 Vol. 31 Apr. 2026 0000-00-00 Zaloznikova Objavljeno apc 0000-00-00 0000-00-00 0000-00-00 547.81 1420-3049 10.3390/molecules31081301 275826691 RAZ_Krivec_Marko_2026.pdf RAZ_Krivec_Marko_2026.pdf 1 A19442774B2CDBDD9170D8FBEF3864EB 0b2b7d133c73872ce891e2c25d14934810496a126b34e5af9d071e382e8213a7 66f618d2-3cae-11f1-b0ab-0050569b8976 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=232758 https://www.mdpi.com/1420-3049/31/8/1301 1 122a6d55-3cae-11f1-b0ab-0050569b8976 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=232757 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0