Proline-based organocatalyst-mediated asymmetric aldol reaction of acetone with substituted aromatic aldehydes: An experimental and theoretical study
Yükleniyor...
Tarih
2020
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
TUBITAK
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
This 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.
Açıklama
Anahtar Kelimeler
Acetone, Aldol reaction, Computational modelling, Enantioselectivity, Organocatalysis, Proline, Substituted aldehydes
Kaynak
Turkish Journal of Chemistry
WoS Q Değeri
Q4
Scopus Q Değeri
Q3
Cilt
44
Sayı
2
Künye
Arslan, 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.
