Proline-based organocatalyst-mediated asymmetric aldol reaction of acetone with substituted aromatic aldehydes: an experimental and theoretical study

Nevin ARSLAN; Selami ERCAN; Necmettin PİRİNÇÇİOĞLU

doi:https://doi.org/10.3906/kim-1908-3

Makale detayları

Proline-based organocatalyst-mediated asymmetric aldol reaction of acetone with substituted aromatic aldehydes: an experimental and theoretical study

Yazarlar:

Nevin ARSLAN | Selami ERCAN | Necmettin PİRİNÇÇİOĞLU

Yayıncı:

TUBITAK

Dergi:

Turkish Journal of Chemistry 2020 Vol.44 Issue 2, pp.335-351

Belge Tipi:

Makale

Yayın Tarihi:

2/2020

Belge Dili:

İngilizce

Document ID (Org No.):

2000725423

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

DOI:

https://doi.org/10.3906/kim-1908-3

Özet:

 

This work involves a facile synthesis of three  S -proline-based organocatalysts with C22_{2}  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 computationaloutcomeswereconsistentwiththoseproducedbyexperimentalresultsandtheywerevaluabletoelucidate the mechanism for the observed stereoselectivity.

Makale detayları

Proline-based organocatalyst-mediated asymmetric aldol reaction of acetone with substituted aromatic aldehydes: an experimental and theoretical study

Yazarlar: Nevin ARSLAN | Selami ERCAN | Necmettin PİRİNÇÇİOĞLU

Yayıncı: TUBITAK

Dergi: Turkish Journal of Chemistry 2020 Vol.44 Issue 2, pp.335-351

Belge Tipi: Makale

Yayın Tarihi: 2/2020

Belge Dili: İngilizce

Document ID (Org No.): 2000725423

Sıklık: İki Aylık

eISSN: 1303-6130

pISSN: 1300-0527

DOI: https://doi.org/10.3906/kim-1908-3

Sayı

Yazarlar:

Nevin ARSLAN | Selami ERCAN | Necmettin PİRİNÇÇİOĞLU

Yayıncı:

TUBITAK

Dergi:

Turkish Journal of Chemistry 2020 Vol.44 Issue 2, pp.335-351

Belge Tipi:

Makale

Yayın Tarihi:

2/2020

Belge Dili:

İngilizce

Document ID (Org No.):

2000725423

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

DOI:

https://doi.org/10.3906/kim-1908-3