How to cite this paper
Kapłon, K., Demchuk, O & Pietrusiewicz, K. (2015). The DFT study on racemisation of atropisomeric biaryls.Current Chemistry Letters, 4(4), 145-152.
Refrences
1 Cepanec I. (2004) Synthesis of biaryls, 1st ed., Elsevier, Amsterdam, Boston.
2 Zhou Q.-L. (2011) Privileged chiral ligands and catalysts, Wiley-VCH, Weinheim.
3 Noyori, R. (1994) Asymmetric catalysis in organic synthesis, Wiley; New York.
4 Kocovsky, P.; Vyskocil, S.; Smrcina, M. (2003) Non-Symmetrically Substituted 1,1’-Binaphthyls in Enantioselective Catalysis, Chem. Rev., 103, 3213-3245.
5 Zhou, Y.; Yang, Q. G. He, Y.; Zhong, H. Z.; Sang, C. He, G. Y.; Liu, W.; Yang, C. H.; Bai, F. L.; Li, Y. F. (2008) Binaphthyl?Containing Green?and Red?Emitting Molecules for Solution?Processable Organic Light?Emitting Diodes, Adv. Funct. Mater., 18, 3299-3306.
6 Bringmann, G.; Mortimer, A. J. P.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. (2005) Atroposelective Synthesis of Axially Chiral Biaryl Compounds, Angew. Chem. Int. Edit., 44, 5384-5427.
7 Demchuk O. M., Kielar K., Pietrusiewicz K. M. (2011) Rational design of novel ligands for environmentally benign cross-coupling reactions. Pure and Appl. Chem. 83, 633-644.
8 Cui Q., Huntley Ch. M., Lemieux R. P. (2009) The detection of chiral perturbations in ferroelectric liquid crystals induced by dopants with axially chiral 2,2?-spirobiindan-1,1?-dione cores. J. Mater. Chem. 19, 5188-5192.
9 Buechi G., Luk K. Ch., Kobbe B., Townsend J. M. (1977) Four new mycotoxins of Aspergillus clavatus related to tryptoquivaline. J. Org. Chem. 42, 244-246.
10 François G., Timperman G., Eling W., Assi L. A., Holenz J., Bringmann G. (1997) Naphthylisoquinoline alkaloids against malaria: evaluation of the curative potentials of dioncophylline C and dioncopeltine A against Plasmodium berghei in vivo. Antimicrob. Agents Chemother. 41, 2533-2539.
11 Kielar K., Demchuk O. M., Pietrusiewicz K. M. (2011) General Approach to the Synthesis of Prochiral Atropisomeric Biaryls. ISRN Organic Chemistry, 2011, 1-11.
12 a) Demchuk O. M., ?astawiecka E., Pietrusiewicz K. M. (2012) Evaluation of efficiency of chiral atropisomeric phosphorus ligands in the asymmetric catalytic processes mediated by transition metal complexes Part 1: Evaluation of steric effects. Chemik, 66, 758-770; b) Demchuk O. M., ?astawiecka E., Pietrusiewicz K. M. (2012) Evaluation of efficiency of chiral atropisomeric phosphorus ligands in the asymmetric catalytic processes mediated by transition metal complexes Part II: An assessment of electron effects. Chemik, 67, 325-340.
13 Demchuk O. M., Arlt D., Jasinski R., Pietrusiewicz K. M. (2012) Relationship between structure and efficiency of atropisomeric phosphine ligands in homogeneous catalytic asymmetric hydrogenation. J. Phys. Org. Chem., 25, 1006-1011.
14 Kielar K., Demchuk O. M., Pietrusiewicz K. M. (2012) Synthesis of Sym-Phos {dicyclohexyl-[3-(2,4,6-trimethoxyphenyl)-4-methoxynaphth-2-yl]phosphine} ligand and its application in Suzuki-Miyaura reaction. Chemik, 66, 585-594.
15 Demchuk O. M., Justyniak I., Miroslaw B., Jasinski R. (2014) 2-Methoxynaphthylnaphthoquinone and its solvate: synthesis and structure-properties relationship. J. Phys. Org. Chem., 27, 66-73.
16 Kyba E. P., Gokel G. W., Dejong F., Koga K., Sousa L. R., Siegel M. G., Kaplan, L., Sogah G. D. Y., Cram D. J. (1977) Host-guest complexation .7. binaphthyl structural unit in host compounds. J. Org. Chem. 42, 4173-4184.
17 Cooke A. S., Harris M. M. (1963) Ground-state strain and other factors influencing optical stability in 1,1 & apos; -binaphthyl series. J. Chem. Soc. 2365-2373.
18 Ling C. C. K., Harris M. M. (1964) Mechanism of Racemisation of [2,2]-Di-Iodobiphenyl. J. Chem. Soc. 1825-1835.
19 Yu J., Cao Y., Song H., Wang X. L., Yao S.(2012) Calculations of optical rotation: Influence of molecular structure. J. Serb. Chem. Soc., 77, 887-898.
20 Jasinski R. (2013) Competition between the one-step and two-step, zwitterionic mechanisms in the [2+3] cycloaddition of gem-dinitroethene with (Z)-C,N-diphenylnitrone: a DFT computational study. Tetrahedron, 69, 927-932.
21 Kap?on K., Demchuk O. M. (2015) Asymmetric synthesis of biaryls. in preparation.
22 Spartan’10, Wavefunction, inc., Irvine, CA.
23 Shao Y. M. L. F., Jung Y., Kussmann J., Ochsenfeld C., Brown S.T., Gilbert A.T.B., Slipchenko L.V., Levchenko S.V., O’neill D.P., Distasio Jr. R.A., Lochan R.C., Wang T., Beran G.J.O., Besley N.A., Herbert J.M., Lin C.Y., Van Voorhis T., Chien S.H., Sodt A., Steele R.P., Rassolov V.A., Maslen P.E., Korambath P.P., Adamson R.D., Austin B., Baker J., Byrd E.F.C., Dachsel H., Doerksen R.J., Dreuw A., Dunietz B.D., Dutoi A.D., Furlani T.R., Gwaltney S.R., Heyden A., Hirata S., Hsu C-P., Kedziora G., Khalliulin R.Z., Klunzinger P., Lee A.M., Lee M.S., Liang W.Z., Lotan I., Nair N., Peters B., Proynov E.I., Pieniazek P.A., Rhee Y.M., Ritchie J., Rosta E., Sherrill C.D., Simmonett A.C., Subotnik J.E.,. Woodcock Iii H.L, Zhang W., Bell A.T., Chakraborty A.K., Chipman D.M., Keil F.J., Warshel A., Hehre W.J., Schaefer H.F., Kong J., Krylov A.I., Gill P.M.W.And Head-Gordon M. (2006) Advances in methods and algorithms in a modern quantum chemistry program package. Phys. Chem. Chem. Phys. 8, 3172-3191.
24 Marenich A. V., Olson R. M., Kelly C. P., Cramer C. J., Truhlar D. G. (2007) Self-consistent reaction field model for aqueous and nonaqueous solutions based on accurate polarized partial charges. J. Chem. Theory. Comput. 3, 2011-2033.
2 Zhou Q.-L. (2011) Privileged chiral ligands and catalysts, Wiley-VCH, Weinheim.
3 Noyori, R. (1994) Asymmetric catalysis in organic synthesis, Wiley; New York.
4 Kocovsky, P.; Vyskocil, S.; Smrcina, M. (2003) Non-Symmetrically Substituted 1,1’-Binaphthyls in Enantioselective Catalysis, Chem. Rev., 103, 3213-3245.
5 Zhou, Y.; Yang, Q. G. He, Y.; Zhong, H. Z.; Sang, C. He, G. Y.; Liu, W.; Yang, C. H.; Bai, F. L.; Li, Y. F. (2008) Binaphthyl?Containing Green?and Red?Emitting Molecules for Solution?Processable Organic Light?Emitting Diodes, Adv. Funct. Mater., 18, 3299-3306.
6 Bringmann, G.; Mortimer, A. J. P.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. (2005) Atroposelective Synthesis of Axially Chiral Biaryl Compounds, Angew. Chem. Int. Edit., 44, 5384-5427.
7 Demchuk O. M., Kielar K., Pietrusiewicz K. M. (2011) Rational design of novel ligands for environmentally benign cross-coupling reactions. Pure and Appl. Chem. 83, 633-644.
8 Cui Q., Huntley Ch. M., Lemieux R. P. (2009) The detection of chiral perturbations in ferroelectric liquid crystals induced by dopants with axially chiral 2,2?-spirobiindan-1,1?-dione cores. J. Mater. Chem. 19, 5188-5192.
9 Buechi G., Luk K. Ch., Kobbe B., Townsend J. M. (1977) Four new mycotoxins of Aspergillus clavatus related to tryptoquivaline. J. Org. Chem. 42, 244-246.
10 François G., Timperman G., Eling W., Assi L. A., Holenz J., Bringmann G. (1997) Naphthylisoquinoline alkaloids against malaria: evaluation of the curative potentials of dioncophylline C and dioncopeltine A against Plasmodium berghei in vivo. Antimicrob. Agents Chemother. 41, 2533-2539.
11 Kielar K., Demchuk O. M., Pietrusiewicz K. M. (2011) General Approach to the Synthesis of Prochiral Atropisomeric Biaryls. ISRN Organic Chemistry, 2011, 1-11.
12 a) Demchuk O. M., ?astawiecka E., Pietrusiewicz K. M. (2012) Evaluation of efficiency of chiral atropisomeric phosphorus ligands in the asymmetric catalytic processes mediated by transition metal complexes Part 1: Evaluation of steric effects. Chemik, 66, 758-770; b) Demchuk O. M., ?astawiecka E., Pietrusiewicz K. M. (2012) Evaluation of efficiency of chiral atropisomeric phosphorus ligands in the asymmetric catalytic processes mediated by transition metal complexes Part II: An assessment of electron effects. Chemik, 67, 325-340.
13 Demchuk O. M., Arlt D., Jasinski R., Pietrusiewicz K. M. (2012) Relationship between structure and efficiency of atropisomeric phosphine ligands in homogeneous catalytic asymmetric hydrogenation. J. Phys. Org. Chem., 25, 1006-1011.
14 Kielar K., Demchuk O. M., Pietrusiewicz K. M. (2012) Synthesis of Sym-Phos {dicyclohexyl-[3-(2,4,6-trimethoxyphenyl)-4-methoxynaphth-2-yl]phosphine} ligand and its application in Suzuki-Miyaura reaction. Chemik, 66, 585-594.
15 Demchuk O. M., Justyniak I., Miroslaw B., Jasinski R. (2014) 2-Methoxynaphthylnaphthoquinone and its solvate: synthesis and structure-properties relationship. J. Phys. Org. Chem., 27, 66-73.
16 Kyba E. P., Gokel G. W., Dejong F., Koga K., Sousa L. R., Siegel M. G., Kaplan, L., Sogah G. D. Y., Cram D. J. (1977) Host-guest complexation .7. binaphthyl structural unit in host compounds. J. Org. Chem. 42, 4173-4184.
17 Cooke A. S., Harris M. M. (1963) Ground-state strain and other factors influencing optical stability in 1,1 & apos; -binaphthyl series. J. Chem. Soc. 2365-2373.
18 Ling C. C. K., Harris M. M. (1964) Mechanism of Racemisation of [2,2]-Di-Iodobiphenyl. J. Chem. Soc. 1825-1835.
19 Yu J., Cao Y., Song H., Wang X. L., Yao S.(2012) Calculations of optical rotation: Influence of molecular structure. J. Serb. Chem. Soc., 77, 887-898.
20 Jasinski R. (2013) Competition between the one-step and two-step, zwitterionic mechanisms in the [2+3] cycloaddition of gem-dinitroethene with (Z)-C,N-diphenylnitrone: a DFT computational study. Tetrahedron, 69, 927-932.
21 Kap?on K., Demchuk O. M. (2015) Asymmetric synthesis of biaryls. in preparation.
22 Spartan’10, Wavefunction, inc., Irvine, CA.
23 Shao Y. M. L. F., Jung Y., Kussmann J., Ochsenfeld C., Brown S.T., Gilbert A.T.B., Slipchenko L.V., Levchenko S.V., O’neill D.P., Distasio Jr. R.A., Lochan R.C., Wang T., Beran G.J.O., Besley N.A., Herbert J.M., Lin C.Y., Van Voorhis T., Chien S.H., Sodt A., Steele R.P., Rassolov V.A., Maslen P.E., Korambath P.P., Adamson R.D., Austin B., Baker J., Byrd E.F.C., Dachsel H., Doerksen R.J., Dreuw A., Dunietz B.D., Dutoi A.D., Furlani T.R., Gwaltney S.R., Heyden A., Hirata S., Hsu C-P., Kedziora G., Khalliulin R.Z., Klunzinger P., Lee A.M., Lee M.S., Liang W.Z., Lotan I., Nair N., Peters B., Proynov E.I., Pieniazek P.A., Rhee Y.M., Ritchie J., Rosta E., Sherrill C.D., Simmonett A.C., Subotnik J.E.,. Woodcock Iii H.L, Zhang W., Bell A.T., Chakraborty A.K., Chipman D.M., Keil F.J., Warshel A., Hehre W.J., Schaefer H.F., Kong J., Krylov A.I., Gill P.M.W.And Head-Gordon M. (2006) Advances in methods and algorithms in a modern quantum chemistry program package. Phys. Chem. Chem. Phys. 8, 3172-3191.
24 Marenich A. V., Olson R. M., Kelly C. P., Cramer C. J., Truhlar D. G. (2007) Self-consistent reaction field model for aqueous and nonaqueous solutions based on accurate polarized partial charges. J. Chem. Theory. Comput. 3, 2011-2033.