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Four types of dienophile\u2013Lewis acid (LA) complexes were considered \u2014 two types of ELA<jats:bold>\u00b7<\/jats:bold>AlCl<jats:sub>3<\/jats:sub>, ELA<jats:bold>\u00b7<\/jats:bold>2AlCl<jats:sub>3<\/jats:sub> and ELA<jats:bold>\u00b7<\/jats:bold>AlCl<jats:sub>2<\/jats:sub><jats:sup>+<\/jats:sup>. The stereochemical predictions of these models were compared with available experimental data. The participation of lactate\u2010bound ELA<jats:bold>\u00b7<\/jats:bold>AlCl<jats:sub>3<\/jats:sub> complexes is insignificant because of their relatively high TS energies. The diastereofacial selectivities exhibited by the chelated ELA<jats:bold>\u00b7<\/jats:bold>AlCl<jats:sub>2<\/jats:sub><jats:sup>+<\/jats:sup> complex do not agree with experimental data, suggesting that this type of complex is not very probable, even with ligands having an appropriate carbonyl orientation. Our results show the dominating role of ELA<jats:bold>\u00b7<\/jats:bold>2AlCl<jats:sub>3<\/jats:sub> in the catalyzed reaction, in agreement with experimental data. The observed diastereofacial stereoselectivities are due to a delicate equilibrium of electrostatic and steric interactions in the different transition states between the two LA groups and between these two groups and the cyclopentadiene moiety. (\u00a9 Wiley\u2010VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2006)<\/jats:p>","DOI":"10.1002\/ejoc.200500809","type":"journal-article","created":{"date-parts":[[2006,1,31]],"date-time":"2006-01-31T10:47:14Z","timestamp":1138704434000},"page":"1779-1789","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["A Theoretical Study of the Stereoselectivities of the Diels\u2013Alder Addition of Cyclopentadiene to Ethyl\u2010(<i>S<\/i>)\u2010lactyl Acrylate Catalyzed by Aluminium Chloride"],"prefix":"10.1002","volume":"2006","author":[{"given":"Snezhana M.","family":"Bakalova","sequence":"first","affiliation":[]},{"given":"A. 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