메뉴 건너뛰기




Volumn 11, Issue 6, 2009, Pages 1401-1404

Enantioselective three-component Kabachnik-Fields reaction catalyzed by chiral scandium(III) N,N'-dioxide complexes

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOPHENOL; 2-AMINOPHENOL; ALDEHYDE; AMINOPHENOL DERIVATIVE; DIPHENYL PHOSPHITE; OXIDE; PHOSPHONIC ACID DERIVATIVE; SCANDIUM;

EID: 64049108750     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9000813     Document Type: Article
Times cited : (67)

References (56)
  • 10
    • 0000899405 scopus 로고
    • For reviews on noncatalytic variants, see: a
    • For reviews on noncatalytic variants, see: (a) Dhawan, B.; Redmore, D. Phosphorus Sulfur 1987, 32, 119.
    • (1987) Phosphorus Sulfur , vol.32 , pp. 119
    • Dhawan, B.1    Redmore, D.2
  • 12
    • 0032562612 scopus 로고    scopus 로고
    • For recent examples of auxiliary-controlled asymmetric hydrophosphonylations, see
    • (c) Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 1998, 9, 1279. For recent examples of auxiliary-controlled asymmetric hydrophosphonylations, see:
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 1279
    • Kolodiazhnyi, O.I.1
  • 14
    • 0034677676 scopus 로고    scopus 로고
    • For reviews on enantioselective catalytic hydrophosphonylations, see: a
    • For reviews on enantioselective catalytic hydrophosphonylations, see: (a) Groger, H.; Hammer, B. Chem. Eur. J. 2000, 6, 943.
    • (2000) Chem. Eur. J , vol.6 , pp. 943
    • Groger, H.1    Hammer, B.2
  • 26
    • 33847309574 scopus 로고    scopus 로고
    • For a one-pot in situ sequence, see
    • For a one-pot in situ sequence, see: Saito, B.; Egami, H.; Katsuki, T. J. Am. Chem. Soc. 2007, 129, 1978.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 1978
    • Saito, B.1    Egami, H.2    Katsuki, T.3
  • 28
    • 49849086423 scopus 로고    scopus 로고
    • Cheng, X.; Goddard, R.; Buth, G.; List, B. Ansew. Chem.. Int. Ed. 2008, 47, 5079.
    • Cheng, X.; Goddard, R.; Buth, G.; List, B. Ansew. Chem.. Int. Ed. 2008, 47, 5079.
  • 30
    • 38049080542 scopus 로고    scopus 로고
    • Zhou, X.; Liu, X. H.; Yang, X.; Shang, D. J.; Xin, J. G.; Feng, X. M. Ansew. Chem.. Int. Ed. 2008, 47, 392.
    • (b) Zhou, X.; Liu, X. H.; Yang, X.; Shang, D. J.; Xin, J. G.; Feng, X. M. Ansew. Chem.. Int. Ed. 2008, 47, 392.
  • 35
    • 2142710085 scopus 로고    scopus 로고
    • For reviews of chiral N-oxides, see: (a) Chelucci, G.; Murineddu, G.; Pinna, G. A. Tetrahedron: Asymmetry 2004, 15, 1373.
    • For reviews of chiral N-oxides, see: (a) Chelucci, G.; Murineddu, G.; Pinna, G. A. Tetrahedron: Asymmetry 2004, 15, 1373.
  • 37
    • 40949126878 scopus 로고    scopus 로고
    • For examples of enantioselective reactions catalyzed by N, N'-dioxide-scandium (III) complexes, see: (a) Shang, D. J, Xin, J. G, Liu, Y. L, Zhou, X, Liu, X. H, Feng, X. M. J. Ors. Chem. 2008, 73, 630
    • For examples of enantioselective reactions catalyzed by N, N'-dioxide-scandium (III) complexes, see: (a) Shang, D. J.; Xin, J. G.; Liu, Y. L.; Zhou, X.; Liu, X. H.; Feng, X. M. J. Ors. Chem. 2008, 73, 630.
  • 39
    • 52649131306 scopus 로고    scopus 로고
    • Kokubo, M.; Ogawa, C; Kobayashi, S. Ansew. Chem.. Int. Ed. 2008, 47, 6909. Chiral N, N'-dioxide-Sc (III) complexes also exhibited excellent asymmetric activating abilities for other carbonyl compounds and bidentate substrates. For selected examples of asymmetric reactions catalyzed by chiral scandium complexes based on other chiral ligands, see:
    • (c) Kokubo, M.; Ogawa, C; Kobayashi, S. Ansew. Chem.. Int. Ed. 2008, 47, 6909. Chiral N, N'-dioxide-Sc (III) complexes also exhibited excellent asymmetric activating abilities for other carbonyl compounds and bidentate substrates. For selected examples of asymmetric reactions catalyzed by chiral scandium complexes based on other chiral ligands, see:
  • 44
    • 0142106406 scopus 로고    scopus 로고
    • For some selected reports in which the chiral scandium complexes chelated with bidentate substrate, see: a
    • For some selected reports in which the chiral scandium complexes chelated with bidentate substrate, see: (a) Yang, D.; Yang, M.; Zhu, N. Y. Ors. Lett. 2003, 5, 3749.
    • (2003) Ors. Lett , vol.5 , pp. 3749
    • Yang, D.1    Yang, M.2    Zhu, N.Y.3
  • 48
    • 64349090920 scopus 로고    scopus 로고
    • 3 was 2:1) was shown to be superior
    • 3 was 2:1) was shown to be superior
  • 49
    • 64349123417 scopus 로고    scopus 로고
    • Aliphatic aldehydes were also investigated. The reactions proceeded smoothly to give the corresponding products with only moderate enantio-selectivities (n-butyraldehyde, 63% yield, 41% ee; cyclohexanecarbaldehyde, 82% yield, 38% ee).
    • (b) Aliphatic aldehydes were also investigated. The reactions proceeded smoothly to give the corresponding products with only moderate enantio-selectivities (n-butyraldehyde, 63% yield, 41% ee; cyclohexanecarbaldehyde, 82% yield, 38% ee).
  • 50
    • 0030788440 scopus 로고    scopus 로고
    • For reviews of lanthanide complexes in asymmetric reactions, see: (a) Shibasaki, M; Sasai, H.; Arai, T. Ansew. Chem., Int. Ed. 1997, 36, 1236.
    • For reviews of lanthanide complexes in asymmetric reactions, see: (a) Shibasaki, M; Sasai, H.; Arai, T. Ansew. Chem., Int. Ed. 1997, 36, 1236.
  • 55
    • 0037020389 scopus 로고    scopus 로고
    • Mikami, K.; Terada, M.; Matsuzawa, H. Ansew. Chem.. Int. Ed. 2002, 41, 3554.
    • (f) Mikami, K.; Terada, M.; Matsuzawa, H. Ansew. Chem.. Int. Ed. 2002, 41, 3554.
  • 56
    • 54649084881 scopus 로고    scopus 로고
    • For N, N-dioxide-La complex catalyzed reaction, see: Yang, X.; Zhou, X.; Lin, L. L.; Chang, L.; Liu, X. H.; Feng, X. M. Ansew. Chem.. Int. Ed. 2008, 47, 7079.
    • (g) For N, N-dioxide-La complex catalyzed reaction, see: Yang, X.; Zhou, X.; Lin, L. L.; Chang, L.; Liu, X. H.; Feng, X. M. Ansew. Chem.. Int. Ed. 2008, 47, 7079.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.