Enantioselective Michael Addition of Nitroalkanes to Nitroalkenes Catalyzed by Chiral Bifunctional Quinine-Based Squaramides

2015-10-26
Kanberoğlu, Esra
Tanyeli, Cihangir
A family of chiral bifunctional acid-/base-type quinine/squaramide organocatalysts is shown to be highly active promoters of the conjugate addition of 1-nitropropane to various trans-β-nitroalkenes. The cooperation of the quinine and the sterically encumbered squaramide moieties catalyzed the Michael addition reactions at 0 °C by using a catalyst loading of only 2 mol % to afford the 1,3-dinitro Michael adducts with excellent enantioselectivity and diastereoselectivity (up to 95 % ee and syn/anti isomers
Asian Journal of Organic Chemistry

Suggestions

Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes
Dengiz, Çağatay; GUTIERREZ, Gregory D.; SWAGER, Timothy M. (American Chemical Society (ACS), 2017-07-21)
The synthesis of a set of naphthazarin-containing polycyclic conjugated hydrocarbons is described herein. Sequential Diels-Alder reactions on a tautomerized naphthazarin core were employed to access the final conjugated systems. Complete conjugation across the backbone can be achieved through complexation with BF2, as observed by (HNMR)-H-1 analysis and UV/vis spectroscopy. Precise synthetic control over the degree of oxidation of naphthazarin quinone Diels-Alder adduct 10 is additionally demonstrated and e...
ANNULATION REACTIONS OF 4-METHOXY-2-PYRONE WITH VARIOUS ACTIVE METHYL COMPOUNDS
Tanyeli, Cihangir (Informa UK Limited, 1989-01-01)
Some phenolic biphenyl compounds have been synthesised via the annulation reactions of 4-methoxy-2- pyrone with various active methyl compounds.
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...
ENANTIOSELECTIVE OXIDATION OF THIOANISOLE TO METYL PHENYL SULFOXIDE BY CHIRAL COMPOUNDS BEARING N-Cl BOND
İPEK, HALİL; Akdağ, Akın (Informa UK Limited, 2015-08-03)
Chiral sulfoxides are used in asymmetric synthesis and are present in various biologically active compounds. Asymmetric synthesis of the sulfoxides has been performed by chiral metal complexes and non-metals containing peroxide and oxide moieties. In this study, a new metal free method has been developed to oxidize thioanisole into methyl phenyl sulfoxide with easily accessible chiral compounds carrying N-Cl bond. For this purpose, chiral amine and amide bearing reagents were synthesized and chlorinated by ...
Chemoenzymatic synthesis of chiral hydroxymethyl cycloalkenols
Şenocak, Deniz; Demir, Ayhan Sıtkı; Department of Chemistry (2004)
Chiral cyclic alkenols with hydroxymethyl functionality are important structural units in many biologically active natural compouds such as prostaglandins, sesquiterpene antiviral agents, pentenomycins, xanthocidin, sarkomycin, etc. 1,3-cycloalkanediones are converted into bicyclic polyoxo derivatives with formaldehyde and trioxane in the presence of Lewis acid. Selective oxidation of the bicyclic compounds by using manganese(III)acetate followed by enzyme-catalyzed kinetic resolution afforded chiral bicycl...
Citation Formats
E. Kanberoğlu and C. Tanyeli, “Enantioselective Michael Addition of Nitroalkanes to Nitroalkenes Catalyzed by Chiral Bifunctional Quinine-Based Squaramides,” Asian Journal of Organic Chemistry, vol. 5, no. 1, pp. 114–119, 2015, Accessed: 00, 2021. [Online]. Available: https://hdl.handle.net/11511/92326.