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Volumn 22, Issue 1 E, 2010, Pages

Conformational equilibria of TADDOL-s in solution investigated by vibrational circular dichroism

Author keywords

conformational analysis; DFT calculations; TADDOL; vibrational circular dichroism

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; AROMATIC COMPOUND; METHYL GROUP; PHENYL GROUP; TADDOL; UNCLASSIFIED DRUG;

EID: 78349255483     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20829     Document Type: Conference Paper
Times cited : (7)

References (24)
  • 1
    • 37649026114 scopus 로고    scopus 로고
    • TADDOLs, their derivatives, and TADDOL analogs: Versatile chiral auxiliaries
    • Seebach D, Beck AK, Heckel A,. TADDOLs, their derivatives, and TADDOL analogs: versatile chiral auxiliaries. Angew Chem Int Ed 2001; 40: 92 138.
    • (2001) Angew Chem Int Ed , vol.40 , pp. 92-138
    • Seebach, D.1    Beck, A.K.2    Heckel, A.3
  • 2
    • 52349086352 scopus 로고    scopus 로고
    • Use of Taddols and their derivatives in asymmetric synthesis
    • Pellisier H,. Use of Taddols and their derivatives in asymmetric synthesis. Tetrahedron 2008; 64: 10279 10317.
    • (2008) Tetrahedron , vol.64 , pp. 10279-10317
    • Pellisier, H.1
  • 3
    • 0026619595 scopus 로고
    • Synthesis and structure of (4R,5R)-a,a,a′,a′-2,2-hexaphenyl- 4,5-dimethanol-1,3-dioxolane
    • Irurre J, Alonso-Alija C, Piniella JF, Alvarez-Larena A,. Synthesis and structure of (4R,5R)-a,a,a′,a′-2,2-hexaphenyl-4,5-dimethanol-1,3- dioxolane. Tetrahedron: Asymmetry 1992; 3: 1591 1596.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 1591-1596
    • Irurre, J.1    Alonso-Alija, C.2    Piniella, J.F.3    Alvarez-Larena, A.4
  • 4
    • 21844520242 scopus 로고
    • Preparation and cationic rearrangements of ortho- and para-methoxy-TADDOLs
    • Seebach D, Rheiner PB, Beck AK, Kuehnle FNM, Jaun B,. Preparation and cationic rearrangements of ortho- and para-methoxy-TADDOLs. Polym J Chem 1994; 68: 2397 2413.
    • (1994) Polym J Chem , vol.68 , pp. 2397-2413
    • Seebach, D.1    Rheiner, P.B.2    Beck, A.K.3    Kuehnle, F.N.M.4    Jaun, B.5
  • 7
    • 0242322522 scopus 로고    scopus 로고
    • Absolute Configuration Determination of Chiral Molecules in the Solution State Using Vibrational Circular Dichroism
    • DOI 10.1002/chir.10287
    • Freedman TB, Cao X, Dukor RK, Nafie LA,. Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism. Chirality 2003; 15: 743 758. (Pubitemid 37356644)
    • (2003) Chirality , vol.15 , Issue.9 , pp. 743-758
    • Freedman, T.B.1    Cao, X.2    Dukor, R.3    Nafie, L.A.4
  • 8
    • 33847373393 scopus 로고    scopus 로고
    • Vibrational absorption and circular dichroism studies of (?)-camphanic acid
    • Buffeteau T, Cavagnat D, Bouchet A, Brotin T,. Vibrational absorption and circular dichroism studies of (?)-camphanic acid. J Phys Chem A 2007; 111: 1045 1051.
    • (2007) J Phys Chem A , vol.111 , pp. 1045-1051
    • Buffeteau, T.1    Cavagnat, D.2    Bouchet, A.3    Brotin, T.4
  • 9
    • 0034063201 scopus 로고    scopus 로고
    • Determination of the structure of chiral molecules using ab initio vibrational circular dichroism spectroscopy
    • Stephens PJ, Delvin FJ,. Determination of the structure of chiral molecules using ab initio vibrational circular dichroism spectroscopy. Chirality 2000; 12: 172 179.
    • (2000) Chirality , vol.12 , pp. 172-179
    • Stephens, P.J.1    Delvin, F.J.2
  • 10
    • 0000992436 scopus 로고
    • Design of a new chiral host compound, trans-4,5- bis(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxacyclopentane. An effective optical resolution of bicyclic enones through host-guest complex formation
    • Toda F, Tanaka K,. Design of a new chiral host compound, trans-4,5-bis(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxacyclopentane. An effective optical resolution of bicyclic enones through host-guest complex formation. Tetrahedron Lett 1988; 29: 551 554.
    • (1988) Tetrahedron Lett , vol.29 , pp. 551-554
    • Toda, F.1    Tanaka, K.2
  • 11
    • 85027983629 scopus 로고    scopus 로고
    • (4R,5R)-2,2-dimethyl-a,a,a′,a′-tetra(naphth-2-yl)-1, 3-dioxolane-4,5-dimethanol from dimethyl tartrate and 2-naphthyl-magnesium bromide (1,3-dioxolane-4,5-dimethanol, 2,2-dimethyl-a,a,a′,a′-tetra- 2-naphthalenyl-, (4R-trans)-)
    • Beck AK, Gysi P, La Vecchia L, Seebach D,. (4R,5R)-2,2-dimethyl-a,a, a′,a′-tetra(naphth-2-yl)-1,3-dioxolane-4,5-dimethanol from dimethyl tartrate and 2-naphthyl-magnesium bromide (1,3-dioxolane-4,5-dimethanol, 2,2-dimethyl-a,a,a′,a′-tetra-2-naphthalenyl-, (4R-trans)-). Org Synth 1999; 76: 12 22.
    • (1999) Org Synth , vol.76 , pp. 12-22
    • Beck, A.K.1    Gysi, P.2    La Vecchia, L.3    Seebach, D.4
  • 12
    • 0001570290 scopus 로고
    • Large-scale preparation of a,a,a′,a′-tetraaryl-1,3-dioxolane- 4,5-dimethanol derivatives (TADDOLs), useful auxiliaries for enantioselective synthesis and their structure in the solid state
    • Beck AK, Bastani B, Plattner DA, Petter W, Seebach D, Braunschweiger H, Gysi P, La Vecchia L,. Large-scale preparation of a,a,a′,a′- tetraaryl-1,3-dioxolane-4,5-dimethanol derivatives (TADDOLs), useful auxiliaries for enantioselective synthesis and their structure in the solid state. Chimia 1991; 45: 238 241.
    • (1991) Chimia , vol.45 , pp. 238-241
    • Beck, A.K.1    Bastani, B.2    Plattner, D.A.3    Petter, W.4    Seebach, D.5    Braunschweiger, H.6    Gysi, P.7    La Vecchia, L.8
  • 13
    • 0000826366 scopus 로고
    • On the Ti-TADDOLate-catalyzed diels-alder addition of 3-butenoyl-1,3-oxazolidin-2-one to cyclopentadiene. General features of Ti-BINOLate- and Ti-TADDOLate-mediated reactions
    • Seebach D, Dahinden R, Marti RE, Beck AK, Plattner DA, Kuhnle FNM,. On the Ti-TADDOLate-catalyzed diels-alder addition of 3-butenoyl-1,3-oxazolidin-2- one to cyclopentadiene. General features of Ti-BINOLate- and Ti-TADDOLate-mediated reactions. J Org Chem 1995; 60: 1788 1799.
    • (1995) J Org Chem , vol.60 , pp. 1788-1799
    • Seebach, D.1    Dahinden, R.2    Marti, R.E.3    Beck, A.K.4    Plattner, D.A.5    Kuhnle, F.N.M.6
  • 14
    • 0034470561 scopus 로고    scopus 로고
    • Highly enantioselective protonation of the 3,4-dihydro-2- methylnaphthalen-1(2H)-one Li-enolate by TADDOLs
    • Cuenca A, Medio-Simon M, Aguilar GA, Weibel D, Beck AK, Seebach D,. Highly enantioselective protonation of the 3,4-dihydro-2-methylnaphthalen-1(2H)- one Li-enolate by TADDOLs. Helv Chim Acta 2000; 83: 3153 3162.
    • (2000) Helv Chim Acta , vol.83 , pp. 3153-3162
    • Cuenca, A.1    Medio-Simon, M.2    Aguilar, G.A.3    Weibel, D.4    Beck, A.K.5    Seebach, D.6
  • 15
    • 21244439487 scopus 로고    scopus 로고
    • Vibrational circular dichroism in general anisotropic thin solid films: Measurement and theoretical approach
    • Buffeteau T, Lagugné-Labarthet F, Sourisseau C,. Vibrational circular dichroism in general anisotropic thin solid films: Measurement and theoretical approach. Appl Spectrosc 2005; 59: 732 745.
    • (2005) Appl Spectrosc , vol.59 , pp. 732-745
    • Buffeteau, T.1    Lagugné-Labarthet, F.2    Sourisseau, C.3
  • 16
    • 0006856135 scopus 로고
    • In: Ferraro J.R., Basile L.J., editors. Fourier transform infrared spectroscopy, Vol. New York: Academic Press
    • Nafie LA, Vidrine DW,. Double modulation fourier transform spectroscopy. In:, Ferraro JR, Basile LJ, editors. Fourier transform infrared spectroscopy, Vol. 3. New York: Academic Press; 1982. pp. 83 123.
    • (1982) Double Modulation Fourier Transform Spectroscopy , vol.3 , pp. 83-123
    • Nafie, L.A.1    Vidrine, D.W.2
  • 17
    • 33745597056 scopus 로고    scopus 로고
    • RM1: A reparameterization of AM1 for H, C, N, O, P, S, F, Cl, Br, and i
    • Rocha GB, Freire IO, Simas AM, Stewart JJP,. RM1: A reparameterization of AM1 for H, C, N, O, P, S, F, Cl, Br, and I. J Comput Chem 2006; 27: 1101 1111.
    • (2006) J Comput Chem , vol.27 , pp. 1101-1111
    • Rocha, G.B.1    Freire, I.O.2    Simas, A.M.3    Stewart, J.J.P.4
  • 18
    • 84990710929 scopus 로고
    • Simulated annealing to locate various stationary points in semiempirical methods
    • Bockisch F, Liotard D, Rayez JC, Duguay B,. Simulated annealing to locate various stationary points in semiempirical methods. Int J Quantum Chem 1992; 44: 619 642.
    • (1992) Int J Quantum Chem , vol.44 , pp. 619-642
    • Bockisch, F.1    Liotard, D.2    Rayez, J.C.3    Duguay, B.4
  • 19
    • 78349267779 scopus 로고    scopus 로고
    • Semichem. KS: Semichem
    • Semichem. AMPAC-8. KS: Semichem, 2004.
    • (2004) AMPAC-8
  • 21
    • 0030580848 scopus 로고    scopus 로고
    • Ab initio calculation of atomic axial tensors and vibrational rotational strengths using density functional theory
    • Cheeseman JR, Frisch MJ, Delvin FJ, Stephens PJ,. Ab initio calculation of atomic axial tensors and vibrational rotational strengths using density functional theory. Chem Phys Lett 1996; 252: 211 220.
    • (1996) Chem Phys Lett , vol.252 , pp. 211-220
    • Cheeseman, J.R.1    Frisch, M.J.2    Delvin, F.J.3    Stephens, P.J.4
  • 23
    • 0001362196 scopus 로고    scopus 로고
    • Reduction of ketones with LiAlH4 complexes of a,a,a′,a′- tetraaryl-1,3-dioxolane-4,5-dimethanols (TADDOLs). A combination of enantioselective reduction and clathrate formation with a discussion of LAH reagents bearing C2-symmetrical ligands
    • Seebach D, Beck AK, Dahinden R, Hoffmann M, Kuehnle FNM,. Reduction of ketones with LiAlH4 complexes of a,a,a′,a′-tetraaryl-1,3-dioxolane- 4,5-dimethanols (TADDOLs). A combination of enantioselective reduction and clathrate formation with a discussion of LAH reagents bearing C2-symmetrical ligands. Croat Chem Acta 1996; 69: 459 484.
    • (1996) Croat Chem Acta , vol.69 , pp. 459-484
    • Seebach, D.1    Beck, A.K.2    Dahinden, R.3    Hoffmann, M.4    Kuehnle, F.N.M.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.