메뉴 건너뛰기




Volumn 129, Issue 17, 2007, Pages 5772-5778

Organocatalytic asymmetric 1,6-additions of β-ketoesters and glycine imine

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC REACTION; BENZOPHENONE IMINE; RING SYSTEMS;

EID: 34247853260     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0707097     Document Type: Article
Times cited : (129)

References (82)
  • 6
    • 34247884846 scopus 로고
    • Trost, B. M, Fleming, L. Eds, Pergamon Press: Oxford, Chapters 1.1-1.6. pp
    • Comprehensive Organic Synthesis; Trost, B. M., Fleming, L. Eds.; Pergamon Press: Oxford, 1991; Vol. 4, Chapters 1.1-1.6. pp 1-268.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 1-268
  • 13
    • 0000679263 scopus 로고    scopus 로고
    • Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer-Verlag: Berlin, Chapter 31, pp
    • (c) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 3, Chapter 31, pp 1105-1142.
    • (1999) Comprehensive Asymmetric Catalysis , vol.3 , pp. 1105-1142
  • 14
    • 0003544583 scopus 로고    scopus 로고
    • 2nd ed, Ojima, I, Ed, Wiley-VCH: Weinheim, Germany
    • (d) Kanai, M.; Shibasaki, M. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: Weinheim, Germany, 2000; p 569.
    • (2000) Catalytic Asymmetric Synthesis , pp. 569
    • Kanai, M.1    Shibasaki, M.2
  • 40
    • 47749122232 scopus 로고    scopus 로고
    • Berkessel, A, Gröger, H, Eds, Wiley-VCH: Weinheim, Germany
    • (c) Asymmetric Organocatalysis; Berkessel, A., Gröger, H., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
    • (2005) Asymmetric Organocatalysis
  • 41
    • 0003544583 scopus 로고    scopus 로고
    • 2nd ed, Ojima, I, Ed, Wiley-VCH: Weinheim, Germany
    • (a) O'Donnell, M. J. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: Weinheim, Germany, 2000; p 727.
    • (2000) Catalytic Asymmetric Synthesis , pp. 727
    • O'Donnell, M.J.1
  • 42
    • 0002855131 scopus 로고    scopus 로고
    • Vogtle, F, Stoddard, J. F, Shibasaki, M, Eds, Wiley-VCH: Weinheim, Germany
    • (b) Shioiri, T.; Arai, S. In Stimulating Concepts in Chemistry; Vogtle, F., Stoddard, J. F., Shibasaki, M., Eds.; Wiley-VCH: Weinheim, Germany, 2000; p 123.
    • (2000) Stimulating Concepts in Chemistry , pp. 123
    • Shioiri, T.1    Arai, S.2
  • 43
    • 0032490960 scopus 로고    scopus 로고
    • For asymmetric PTC transformations of β-ketoesters, see: a
    • For asymmetric PTC transformations of β-ketoesters, see: (a) Manabe, K. Tetrahedron Lett. 1998, 39, 5807.
    • (1998) Tetrahedron Lett , vol.39 , pp. 5807
    • Manabe, K.1
  • 52
    • 0002076066 scopus 로고    scopus 로고
    • For reviews on the use of 2 for asymmetric transformations under PTC, see: (a) O'Donnell, M. J. Aldrichimica Acta 2001, 34, 3.
    • For reviews on the use of 2 for asymmetric transformations under PTC, see: (a) O'Donnell, M. J. Aldrichimica Acta 2001, 34, 3.
  • 59
    • 34247899502 scopus 로고    scopus 로고
    • 2O-promoted dehydration (see the Supporting Information).
    • 2O-promoted dehydration (see the Supporting Information).
  • 62
    • 34247880794 scopus 로고    scopus 로고
    • This model was developed on the basis of an X-ray crystallographic analysis of catalyst 6 bearing p-nitrophenolate as the counterion. See ref 12h
    • This model was developed on the basis of an X-ray crystallographic analysis of catalyst 6 bearing p-nitrophenolate as the counterion. See ref 12h.
  • 63
    • 0001866893 scopus 로고    scopus 로고
    • For a review on the synthesis and applications of bicyclo[3.2.1]octanes, see: (a) Filippini, M.-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27.
    • For a review on the synthesis and applications of bicyclo[3.2.1]octanes, see: (a) Filippini, M.-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27.
  • 64
    • 0038294333 scopus 로고    scopus 로고
    • For recent approaches, see, for example: b
    • For recent approaches, see, for example: (b) Kim, J. N.; Kim, J. M.; Lee, K. Y. Synlett 2003, 821.
    • (2003) Synlett , pp. 821
    • Kim, J.N.1    Kim, J.M.2    Lee, K.Y.3
  • 67
    • 27544474635 scopus 로고    scopus 로고
    • Hamashima, Y.; Hotta, D.; Umebayashi, N.; Tsuchiya, Y.; Suzuki, T.; Sodeoka, M. Adv. Synth. Catal. 2005, 347, 1576. See also ref 9b.
    • (e) Hamashima, Y.; Hotta, D.; Umebayashi, N.; Tsuchiya, Y.; Suzuki, T.; Sodeoka, M. Adv. Synth. Catal. 2005, 347, 1576. See also ref 9b.
  • 69
    • 85122201594 scopus 로고    scopus 로고
    • For a comprehensive review on the use of cinchona alkaloids in asymmetric synthesis, see
    • For a comprehensive review on the use of cinchona alkaloids in asymmetric synthesis, see: Kacprzak, K.; Gawronski, J. Synthesis 2001, 961.
    • (2001) Synthesis , pp. 961
    • Kacprzak, K.1    Gawronski, J.2
  • 75
    • 34247897587 scopus 로고    scopus 로고
    • It should be noted that 6 and 6′ are less effective catalysts compared to 8 and 8′, giving the catalytic product in very low yield. This observation could be justified considering the bulkiness of the adamantoyl group, which might prevent an efficient interaction between the sterically demanding enolate derived from 2 and the quaternary nitrogen. In fact, in the solid state a p-nitrophenolate counterion in catalyst 6 was found to be in a different position with respect to the quaternary nitrogen, compared to the same counterion in catalyst 8′, presumably due to the steric effects exerted by the adamantoyl group. For a discussion see ref 12h
    • It should be noted that 6 and 6′ are less effective catalysts compared to 8 and 8′, giving the catalytic product in very low yield. This observation could be justified considering the bulkiness of the adamantoyl group, which might prevent an efficient interaction between the sterically demanding enolate derived from 2 and the quaternary nitrogen. In fact, in the solid state a p-nitrophenolate counterion in catalyst 6 was found to be in a different position with respect to the quaternary nitrogen, compared to the same counterion in catalyst 8′, presumably due to the steric effects exerted by the adamantoyl group. For a discussion see ref 12h.
  • 76
    • 34247857982 scopus 로고    scopus 로고
    • In the case of 5a and 5c, a small amount <10, of the corresponding α,β-unsaturated compounds was detected in the crude mixture, when 50% KOH was used as the base, which could be separated by chromatography from the major γ,δ-unsaturated compounds in both cases
    • In the case of 5a and 5c, a small amount (<10%) of the corresponding α,β-unsaturated compounds was detected in the crude mixture, when 50% KOH was used as the base, which could be separated by chromatography from the major γ,δ-unsaturated compounds in both cases.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.