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Volumn 8, Issue 5, 1997, Pages 673-676

Oxazaborolidine-mediated reduction of prochiral 2-alkylidene cycloalkanones

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; CYCLOALKANOL DERIVATIVE;

EID: 0031053524     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00034-7     Document Type: Article
Times cited : (17)

References (28)
  • 3
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    • The electronic influence of remote substituents is important in oxazaborolidine-mediated reductions. (a) Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1995, 36, 9153-9156.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 9153-9156
    • Corey, E.J.1    Helal, C.J.2
  • 6
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    • (b) Use of yeast as reductant in the preparation of 2b (99% e.e.), see Fronza, G.; Fogliato, G.; Fuganti, C.; Lanati, S.; Rallo, R.; Servi, S. Tetrahedron Lett. 1995, 36, 123-124; Fronza, G.; Fogliato, G.; Fuganti, C.; Lanati, S.; Rallo, R.; Rigoni, R.; Servi, S. Tetrahedron 1995, 51, 10231-10240. Only the absolute stereochemistry of 2b has been established unambiguously.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 123-124
    • Fronza, G.1    Fogliato, G.2    Fuganti, C.3    Lanati, S.4    Rallo, R.5    Servi, S.6
  • 7
    • 0029145276 scopus 로고
    • (b) Use of yeast as reductant in the preparation of 2b (99% e.e.), see Fronza, G.; Fogliato, G.; Fuganti, C.; Lanati, S.; Rallo, R.; Servi, S. Tetrahedron Lett. 1995, 36, 123-124; Fronza, G.; Fogliato, G.; Fuganti, C.; Lanati, S.; Rallo, R.; Rigoni, R.; Servi, S. Tetrahedron 1995, 51, 10231-10240. Only the absolute stereochemistry of 2b has been established unambiguously.
    • (1995) Tetrahedron , vol.51 , pp. 10231-10240
    • Fronza, G.1    Fogliato, G.2    Fuganti, C.3    Lanati, S.4    Rallo, R.5    Rigoni, R.6    Servi, S.7
  • 10
    • 33845280252 scopus 로고
    • (c) Corey, E. J.; Shibati, S.; Bakshi, R. K. J. Org. Chem. 1988, 53, 2861-2863. For synthetic applications of 3 see ref. 2a and for a review on the use of oxazaborolidines in asymmetric synthesis, see Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475-1504.
    • (1988) J. Org. Chem. , vol.53 , pp. 2861-2863
    • Corey, E.J.1    Shibati, S.2    Bakshi, R.K.3
  • 11
    • 0026733927 scopus 로고
    • (c) Corey, E. J.; Shibati, S.; Bakshi, R. K. J. Org. Chem. 1988, 53, 2861-2863. For synthetic applications of 3 see ref. 2a and for a review on the use of oxazaborolidines in asymmetric synthesis, see Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475-1504.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 1475-1504
    • Wallbaum, S.1    Martens, J.2
  • 18
  • 21
    • 0342576796 scopus 로고    scopus 로고
    • note
    • 2 (0.3 mL) at -20°C. After completion of reaction (1 to 1.5 h), cold methanol (3 mL) was added and the solution was then stirred for 1 h. Concentration in vacuo followed by rapid flash chromatography (90:10 hexane:EtOAc) gave allylic alcohols 2.
  • 22
    • 0028220644 scopus 로고
    • For the effect of temperature on the efficiency of oxazaborolidine reductions, see Stone, G. B. Tetrahedron: Asymmetry 1994, 5, 465-472. For further mechanistic studies, see Douglas, A. W.; Tschaen, D. M.; Reamer, R. A.; Shi, Y. J. Tetrahedron: Asymmetry 1996, 7, 1303-1308.
    • (1994) Tetrahedron: Asymmetry , vol.5 , pp. 465-472
    • Stone, G.B.1
  • 23
    • 0030000283 scopus 로고    scopus 로고
    • For the effect of temperature on the efficiency of oxazaborolidine reductions, see Stone, G. B. Tetrahedron: Asymmetry 1994, 5, 465-472. For further mechanistic studies, see Douglas, A. W.; Tschaen, D. M.; Reamer, R. A.; Shi, Y. J. Tetrahedron: Asymmetry 1996, 7, 1303-1308.
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 1303-1308
    • Douglas, A.W.1    Tschaen, D.M.2    Reamer, R.A.3    Shi, Y.J.4
  • 25
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    • 4a (also Evans, D. A. Science 1988, 240, 420) and chair transition states have been suggested for the delivery of hydride. For computational studies on the possible role of a chair transition state see Jones, D. K.; Liotta, D. C.; Shinkai, I.; Mathre, D. J. J. Org. Chem. 1993, 58, 799-781; Linney, L. P.; Self, C. R.; Williams, I. H. J. Chem. Soc., Chem. Commun. 1994, 1651-2.
    • (1988) Science , vol.240 , pp. 420
    • Evans, D.A.1
  • 26
    • 0001752772 scopus 로고
    • 4a (also Evans, D. A. Science 1988, 240, 420) and chair transition states have been suggested for the delivery of hydride. For computational studies on the possible role of a chair transition state see Jones, D. K.; Liotta, D. C.; Shinkai, I.; Mathre, D. J. J. Org. Chem. 1993, 58, 799-781; Linney, L. P.; Self, C. R.; Williams, I. H. J. Chem. Soc., Chem. Commun. 1994, 1651-2.
    • (1993) J. Org. Chem. , vol.58 , pp. 799-1781
    • Jones, D.K.1    Liotta, D.C.2    Shinkai, I.3    Mathre, D.J.4
  • 27
    • 37049079876 scopus 로고
    • 4a (also Evans, D. A. Science 1988, 240, 420) and chair transition states have been suggested for the delivery of hydride. For computational studies on the possible role of a chair transition state see Jones, D. K.; Liotta, D. C.; Shinkai, I.; Mathre, D. J. J. Org. Chem. 1993, 58, 799-781; Linney, L. P.; Self, C. R.; Williams, I. H. J. Chem. Soc., Chem. Commun. 1994, 1651-2.
    • (1994) J. Chem. Soc., Chem. Commun. , pp. 1651-1652
    • Linney, L.P.1    Self, C.R.2    Williams, I.H.3
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    • note
    • 3b, the other allylic alcohols described in this paper have not previously been described in enantiomerically enriched form. All new compounds have been fully characterised.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.