Synthesis of n-(2-propylphenyl) substituted chiral amino alcohols and their usage in enantioselective diethylzinc addition reactions

Günler, Zeynep İnci
IChiral 1,2-amino alcohols were synthesized via newly developed “intramolecular unsaturation transfer” using cyclohexanone, propargyl bromide, and various chiral amino alcohols as starting components. These amino alcohols can be potential chiral ligands for many asymmetric transformation reactions. Therefore, their effectiveness as chiral ligands in diethylzinc addition to benzaldehyde and N-diphenylphosphinoyl imines were tested. Various parameters including temperature, solvent, ligand amount etc. were screened for the synthesized chiral ligands. In diethylzinc addition to benzaldehyde high enantioselectivity could not be obtained. When N-diphenylphosphinoyl imines were used as substrate good ee values up to 80% were achieved.


Synthesis of tertiary propargylic phosphonates by addition of trialkynylaluminum reagents to acyl phosphonates and investigation of their antimicrobial activities
Hossain, Mohammad Shakhawoat; POLAT ÇAKIR, SIDIKA; Karaduman, Ayse Betul; YAMAÇ, MUSTAFA; Demir, Ayhan Sıtkı (2014-01-01)
A series of propargylic alcohols containing phosphonates was synthesized by addition reactions of tris-(propynyl) and tris-(phenylethynyl) aluminum reagents to acyl phosphonates in good yields. Aromatic moieties of the acyl phosphonates with electron-withdrawing groups generally resulted in better isolated chemical yield. Selected propargylic phosphonates were tested for antimicrobial activities. Compounds 3a and 3h showed noticeable antifungal activity, especially against molds.
Synthesis of chiral acetoxy lactones via the Baeyer-Villiger oxidation of cyclic aromatic acetoxy ketones
Demir, Ayhan Sıtkı; Aybey, Asuman (Elsevier BV, 2008-12-01)
The alpha-acetoxylation of indanones and tetralones by using Mn(OAc)(3) followed by the enzyme catalyzed kinetic resolution of acetoxy ketones furnished both of the enantiomers of alpha-acetoxy ketones in good chemical and optical yields. The Baeyer-Villiger oxidation of alpha-acetoxy ketones with m-CPBA, CF(3)SO(3)H, and CH(2)O(2), at rt gives the corresponding lactones without racemization. The acetoxy ketone moiety migrates selectively in order to form lactones. The mild hydrolysis of lactones affords ph...
Synthesis and photooxygenation of homochiral 2-methylpyrrole derivatives of chiral amino alcohols: simple, selective access to chiral bicyclic lactams
Aydogan, F; Demir, Ayhan Sıtkı (2004-01-26)
Homochiral 2-methylpyrrole derivatives are synthesized in high yields starting from chiral amino alcohols and 5-chloro-3-pentene-2-one. The photooxygenation of these compounds in the presence of a photosynthesizer furnishes the pyrrolooxazolone structures in high diastereoselectivities. In all of the examples, trans-isomers are formed as the major products.
Synthesis and characterization of conducting copolymers of poly(vinyl alcohol) with thiophene side-groups and pyrrole
Sahmetlioglu, E; Yuruk, H; Toppare, Levent Kamil; Cianga, I; Yagci, Y (2004-12-01)
Graft copolymers of poly(vinyl alcohol) with thiophene side-groups and pyrrole were synthesized by electrochemical polymerization methods. Poly(vinyl alcohol) with thiophene side-groups (PVATh) was obtained from the reaction between poly(vinyl alcohol) (PVA) and thiophene-3-acetic acid. The syntheses of copolymers Of PVATh and pyrrole were achieved electrochemically by using three different supporting electrolytes, p-toluene sulfonic acid (PTSA), sodium dodecyl sulfate (SDS) and tetrabutylammonium tetrafluo...
Chemistry of bicyclic endoperoxides derived from dihydropyridine derivatives: Attempted synthesis of polyhydroxypiperidine derivatives
Salamci, Emine; Bayram, Beyhan; Balcı, Metin (2006-01-01)
To achieve the synthesis of azasugar derivatives with the utilization of singlet oxygen, pyridine was used as the starting material. The reduction of pyridine followed by a singlet oxygen reaction afforded cyclic aza-endoperoxides (14 and 16). However, many attempts were made to convert the azaendoperoxides to the corresponding di- and triacetates without success. However, the base-catalyzed rearrangement of 14 gave unprecedented rearrangement products 23 and 24.
Citation Formats
Z. İ. Günler, “Synthesis of n-(2-propylphenyl) substituted chiral amino alcohols and their usage in enantioselective diethylzinc addition reactions,” M.S. - Master of Science, Middle East Technical University, 2011.