Arslan, NevinErcan, SelamiPirinççi̇oğlu, Necmettin2021-08-252021-08-252020Arslan, N., Ercan, S. ve Pirinççi̇oğlu, N. (2020). Proline-based organocatalyst-mediated asymmetric aldol reaction of acetone with substituted aromatic aldehydes: An experimental and theoretical study. Turkish Journal of Chemistry, 44(2), 335-351.1300-05271303-6130https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7671204/https://hdl.handle.net/11468/7384https://search.trdizin.gov.tr/yayin/detay/335244This work involves a facile synthesis of three (S)-proline-based organocatalysts with C2 symmetry and their effects in enantioselective aldol reaction of acetone with substituted aromatic aldehydes. Moderate enantioselectivities (up to 61% ee) were obtained depending on the nature of the substituents on the aryl ring. Computational calculations at HF/6-31 + G(d) level were employed to underline the enantioselectivity imposed by all the organocatalysts. Higher calculations at B3LYP/6-311 ++ G(d,p) scrf=(solvent=dichloromethane)//B3LYP/6-31 + G(d) levels of theory were also performed for the aldol reaction of acetone with benzaldehyde and 4-nitrobenzaldehyde catalyzed by 1. The computational outcomes were consistent with those produced by experimental results and they were valuable to elucidate the mechanism for the observed stereoselectivity.eninfo:eu-repo/semantics/openAccessAcetoneAldol reactionComputational modellingEnantioselectivityOrganocatalysisProlineSubstituted aldehydesArticle442335351WOS:0005227960000062-s2.0-850853750893352443348816110.3906/KIM-1908-3Q3Q4