Enantioselective reduction of ketones with borane catalyzed by cyclic β- amino alcohols prepared from proline

Demir, Ayhan S
Mecitoglu, Idris
Tanyeli, Cihangir
Gülbeyaz, Volkan
New catalysts have been prepared from (S)- and (R)- proline and the asymmetric borane reduction of prochiral ketones using these catalysts has been studied. The secondary alcohols were obtained in 76-95% yield with 57-96% enantiomeric excesses. Copyright (C) 1996 Elsevier Science Ltd
Tetrahedron: Asymmetry


Enantioselective synthesis of 4,5,6,7-tetrahydro-4-oxo-benzofuran-5-yl acetate and 1-benzyl-4,5,6,7-tetrahydro-4-oxo-1(H)-indol-5-yl acetate using chemoenzymatic methods
Demir, Ayhan Sıtkı; Caliskan, Zerrin; Sahin, Ertan (Elsevier BV, 2007-03-01)
The chemoenzymatic synthesis of both of the enantiomers of pharmacologically interesting compounds such as 4,5,6,7-tetrahydro-4-oxobenzofuran-5-yl acetate (2a), 4,5,6,7-tetrahydro-4-oxo-6,6-dimethylbenzofuran-5-yl acetate (2b), and their hydroxy derivatives 3a, 3b, 1-benzyl4,5,6,7-tetrahydro-4-oxo-1(H)-indol-5-yl acetate (5), starting from 6,7-dihydrobenzofuran-4(5H)-one (la), 6,7-dihydro-6,6-dimethylbenzofuran4(5H)-one (7b), and 1-benzyl-6,7-dihydro-1 H-indol-4(5H)-one (4) are reported. Manganese(III) acet...
Asymmetric synthesis of N-aryl substituted chiral 1,4-aminoalcohol derivatives and applications in various asymmetric transformation reactions
Odabaş, Serhat; Tanyeli, Cihangir; Department of Chemistry (2007)
The asymmetric synthesis of N-aryl substituted chiral 1,4-aminoalcohols and their applications in asymmetric borane reduction and enantioselective diethylzinc addition to benzaldehyde reactions were performed starting from meso-anhydride 51 that is the cycloadduct of cyclopentadiene and maleic anhydride. The desymmetrization of meso-anhydride 51 was achieved by using quinine or quinidine with very high enantiomeric excess value (up to 98% ee) and with high chemical yield. The quinine-mediated desymmetrizati...
Aryl butenoic acid derivatives as a new class of histone deacetylase inhibitors: synthesis, in vitro evaluation, and molecular docking studies
Esiyok, Peruze Ayhan; Seven, Ozlem; Eymur, Guluzar; Tatar, Gamze Bora; DAYANGAÇ ERDEN, DİDEM; YELEKÇİ, Kemal; YURTER, HAYAT; Demir, Ayhan Sıtkı (The Scientific and Technological Research Council of Turkey, 2014-01-01)
New aryl butenoic acid derivatives have been synthesized by combining hydroxy- or methoxy-substituted phenyl rings as the capping group, with a double bond in the short linker as well as metal binding groups, enoic ester, and salts bearing either methyl or morpholine. These compounds have been shown to possess promising histone deacetylase inhibition activities via in vitro fluorometric assay and molecular docking studies.
Enantioselective synthesis of both enantiomers of 2-amino-2-(2-furyl)ethan-1-ol as a flexible building block for the preparation of serine and azasugars
Demir, Ayhan Sıtkı; Sesenoglu, O; Aksoy-Cam, H; Kaya, H; Aydogan, K (Elsevier BV, 2003-05-16)
The selective conversion of 1-(2-furyl)-2-hydroxyethan-1-one and ethyl 2-(2-furyl)-2-oxo acetate into (E)- and (Z)-oximes and oxime ethers followed by oxazaborolidine-catalyzed enantioselective reduction using different amino alcohols furnished both enantiomers of the important chiral building block 2-amino-2-(2-furyl)ethan-1-ol with an ee of up to 96%.
NiMoS/gamma-Al2O3 catalysts: The nature and the aging behavior of active sites in HDN reactions
ZHANG, LEE P; Karakaş, Gürkan; OZKAN, UMIT S (Elsevier BV, 1998-09-10)
The work presented in this paper is a continuation of our earlier work aimed at acquiring a fundamental understanding of sulfided Ni-Mo/gamma-Al2O3 catalysts in HDN catalysis, A series of temperature-programmed desorption and reduction experiments were performed over in-situ sulfided bare gamma-alumina support, alumina-supported monometallic Ni, Mo, and bimetallic NiMo catalysts. The TPD and TPR results were linked to the active site assignment of Ni- and Mo-associated centers in HDN reactions. Postreaction...
Citation Formats
A. S. Demir, I. Mecitoglu, C. Tanyeli, and V. Gülbeyaz, “Enantioselective reduction of ketones with borane catalyzed by cyclic β- amino alcohols prepared from proline,” Tetrahedron: Asymmetry, pp. 3359–3364, 1996, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/28382.