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Volumn 10, Issue 18, 2008, Pages 4101-4104

Highly practical catalytic asymmetric 1,4-addition of arylboronic acids in water using new hydrophilic chiral bicyclo[3.3.0] diene ligands

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BICYCLO COMPOUND; BORONIC ACID DERIVATIVE; LIGAND; WATER;

EID: 55949107039     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801665z     Document Type: Article
Times cited : (85)

References (42)
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    • For reviews, see: a
    • For reviews, see: (a) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
    • (2003) Chem. Rev , vol.103 , pp. 169
    • Fagnou, K.1    Lautens, M.2
  • 24
    • 4544236676 scopus 로고    scopus 로고
    • For two leading reviews on chiral diene ligands in asymmetric catalysis, see: a
    • For two leading reviews on chiral diene ligands in asymmetric catalysis, see: (a) Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 3364.
    • (2004) Angew. Chem., Int. Ed , vol.43 , pp. 3364
    • Glorius, F.1
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    • Defieber, C.; Grützmacher, H.; Carreira, E. M. Angew. Chem., Int. Ed. 2008, 47, 4482.
    • (b) Defieber, C.; Grützmacher, H.; Carreira, E. M. Angew. Chem., Int. Ed. 2008, 47, 4482.
  • 26
    • 0141450342 scopus 로고    scopus 로고
    • For examples of Rh-diene catalysis in asymmetric 1,4-addition, see: (a) Hayashi, T, Ueyama, K, Tokunaga, N, Yoshida, H. J. Am. Chem. Soc. 2003, 125, 11508
    • For examples of Rh-diene catalysis in asymmetric 1,4-addition, see: (a) Hayashi, T.; Ueyama, K.; Tokunaga, N.; Yoshida, H. J. Am. Chem. Soc. 2003, 125, 11508.
  • 36
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    • Feng, C.-G.; Wang, Z.-Q.; Tian, P.; Xu, M.-H; Lin, G.-Q. Chem. Asian J. 2008, 3, in press (published online May 7. 2008).
    • (b) Feng, C.-G.; Wang, Z.-Q.; Tian, P.; Xu, M.-H; Lin, G.-Q. Chem. Asian J. 2008, 3, in press (published online May 7. 2008).
  • 38
    • 61349157607 scopus 로고    scopus 로고
    • Prepared from the corresponding (1S,3aR,4S,6aR)-octahydropentalene-1,4- diol using the method reported in ref 8.
    • Prepared from the corresponding (1S,3aR,4S,6aR)-octahydropentalene-1,4- diol using the method reported in ref 8.
  • 40
    • 61349198499 scopus 로고    scopus 로고
    • 2O.
    • 2O.
  • 41
    • 61349145915 scopus 로고    scopus 로고
    • Crystallographic data for (R,R)-5 (C12H 14O2, T, 293 (2) K; wavelength: 0.71073 Å; crystal system: orthorhombic, space group: mdit > P212 121; unit cell dimensions: a, 6.1336(7) Å, b, 11.7280(14) Å, c, 14.5571(17) Å, α, 90°, β, 90°, γ, 90°; V, 1047.2 (2) Å3; Z, 4; ρcalc, 1.410 Mg/m3; F(000, 472; final R indices [I > 2σ(I, R 1, 0.0392, wR2, 0.0616; R indices (all data, R1, 0.0564, wR2, 0.0655; 6189 reflections mesured, 1337 were unique (Rint, 0.0711
    • int) = 0.0711).
  • 42
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    • The rhodium complex was obtained by treatment of (R,R)-5 with [RhCl(C2H4)2]2 in THF at room temperature for 48 h. 1H NMR (300 MHz, CDCl3, δ 1.76 (s, 2H, 3.74-3.79 (m, 2H, 3.89 (dd, J, 6.5, 14.0 Hz, 2H, 4.01-4.17 (m, 4H, 4.19-4.30 (m, 4H, 13C NMR (75 MHz, CDCl3, δ 48.1, 65.4, 65.6, 68.0, 68.1, 82.3, 82.4, 119.6. Crystallographic data for [RhCl(R,R)-5]2 (C24H 28Cl2O8Rh2, T, 293(2) K; wavelength: 0.71073 Å; crystal system: orthorhombic, space group: P212121; unit cell dimensions: a, 9.7534(10) Å, b, 9.9312(10) Å, c, 28.882(3) Å, α, 90°, β, 90°, γ, 90°; V, 2797.6(5) Å3; Z, 4; ρcalc, 1.848 Mg/m 3; F000, 1572; f
    • int) = 0.0938).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.