A method for the synthesis of pyridine-based C-2-symmetrical chiral nucleophilic organocatalysts via Pd-catalyzed coupling

Yazicioglu, Emre Y.
Tanyeli, Cihangir
A one step Pd-catalyzed coupling methodology involving a reaction between a chiral diamine and a 2-bromo-4-(alkylamino)pyridine, was developed for the synthesis of novel C-2-symmmetrical chiral compounds with chemical yields of up to 87%. The organocatalytic performance was tested as an alternative to the enzymatic kinetic resolution of 1-phenylethanol and a promising result of 76% ee was obtained. We observed that the catalysts synthesized had their own characteristics in terms of enantioselectivity; for example, non-nucleophilic heterogeneous auxiliary bases and ether solvents proved to be more efficient.


Efficient synthesis of ferrocenylenones by Friedel-Crafts acylation with EtAlCl2-Me3Al
Efficient synthesis of ferrocenyl en ones using a Friedel-Crafts acylation reaction is described. Acryloyl, methacryloyl, crotonoyl, cinnamoyl, and beta-methylcrotonoyl chlorides react with ferrocene in the presence of a Lewis acid (EtAlC2 or EtAlCl2-Me3Al) to give the corresponding ferrocenyl en ones (acryloyl, methacryloyl, crotonoyl, cinnamoyl, and methylcrotonoylferrocenes) in good isolated yields. Besides ferrocenylenones, chloroactylferrocene is also synthesised by this method.
A new and efficient chemoenzymatic route to both enantiomers of alpha '-acetoxy and alpha '-hydroxy-alpha-methoxy cyclic enones
Demir, Ayhan Sıtkı; Caliskan, Z; Aydin, AE; Bicer, I (Elsevier BV, 2006-03-06)
A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting alpha'-acetoxy and alpha'-hydroxy-alpha-methoxy cyclic enones starting from alpha-hydroxy cyclic enones is described. Protection of 1,2-diketones, manganese(III) acetate-mediated acetoxylation followed by enzyme-mediated hydrolysis of alpha'-acetoxy enones gives acetoxy enones 3a-d and hydroxy enones 4a-d with high enantiomeric excesses (up to 99%) and good yields. The transesterification of rac-4b in the presence of DMAP af...
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Tez, Serdar; Torunbalci, Mustafa Mert; Akın, Tayfun (2016-11-03)
This paper presents a novel method for the fabrication of three-axis capacitive MEMS accelerometers by using low-temperature Au-Sn eutectic bonding that is applied to form a glass-silicon-glass multi-stack. The proposed method provides the implementation of individual in-plane and out-of-plane accelerometer elements in the same die using a glass-silicon-glass multi-stack structure formed at temperatures as low as 300 degrees C while still ensuring the advantages of the previous approaches such as the voltag...
A density functional theory study of partial oxidation of propylene on Cu2O(001) and CuO(001) surfaces
Duzenli, Derya; Atmaca, Deniz Onay; Gezer, Miray Gulbiter; Önal, Işık (2015-11-15)
This work theoretically investigates propylene epoxidation reaction on Cu2O(001) and CuO(001) surfaces using periodical DFT method to determine the active copper species within the reaction mechanism. The transition states and energy profiles are calculated for the formation of surface intermediates such as oxametallopropylene (OMP) over Cu2O(0 0 1) and oxygen bridging (OB) over CuO(0 0 1) and allylic H-stripping reaction (AHS) over both surfaces as well as for formation of products. Propylene oxide (PO) an...
An empirical method for the second viral coefficients of non-standard fluids
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Citation Formats
E. Y. Yazicioglu and C. Tanyeli, “A method for the synthesis of pyridine-based C-2-symmetrical chiral nucleophilic organocatalysts via Pd-catalyzed coupling,” TETRAHEDRON-ASYMMETRY, pp. 1694–1699, 2012, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/42128.