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Volumn 125, Issue 36, 2003, Pages 10893-10898

1,5-Asymmetric induction in boron-mediated β-alkoxy methyl ketone aldol addition reactions

Author keywords

[No Author keywords available]

Indexed keywords

STEREOCHEMICAL CONTROL;

EID: 0041733422     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027640h     Document Type: Article
Times cited : (91)

References (36)
  • 1
    • 0028071712 scopus 로고
    • For general approaches to the synthesis of 1,3-diol relationships in conjunction with C-C bond formation, see: (a) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753-1765. (b) Mori, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299-5314. (c) Knochel, P.; Brieden, W.; Rozema, M. J.; Eisenberg, C. Tetrahedron Lett. 1993, 34, 5881-5884.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 1753-1765
    • Rychnovsky, S.D.1    Hoye, R.C.2
  • 2
    • 0028934744 scopus 로고
    • For general approaches to the synthesis of 1,3-diol relationships in conjunction with C-C bond formation, see: (a) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753-1765. (b) Mori, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299-5314. (c) Knochel, P.; Brieden, W.; Rozema, M. J.; Eisenberg, C. Tetrahedron Lett. 1993, 34, 5881-5884.
    • (1995) Tetrahedron , vol.51 , pp. 5299-5314
    • Mori, Y.1    Asai, M.2    Okumura, A.3    Furukawa, H.4
  • 3
    • 0027258013 scopus 로고
    • For general approaches to the synthesis of 1,3-diol relationships in conjunction with C-C bond formation, see: (a) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753-1765. (b) Mori, Y.; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299-5314. (c) Knochel, P.; Brieden, W.; Rozema, M. J.; Eisenberg, C. Tetrahedron Lett. 1993, 34, 5881-5884.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 5881-5884
    • Knochel, P.1    Brieden, W.2    Rozema, M.J.3    Eisenberg, C.4
  • 4
    • 0001091444 scopus 로고
    • and references therein
    • Reetz, M. T. Acc. Chem. Res. 1993, 26, 462-468 and references therein.
    • (1993) Acc. Chem. Res. , vol.26 , pp. 462-468
    • Reetz, M.T.1
  • 12
    • 0042292102 scopus 로고    scopus 로고
    • note
    • A detailed discussion of the procedures that were followed for the assignment of the aldol-related stereochemical relationships is contained in the Supporting Information.
  • 13
    • 0042793054 scopus 로고    scopus 로고
    • note
    • Based on dielectric constants, it is not clear why the more polar diethyl ether (e = 4.3) is a better solvent than toluene (e = 2.4). However, ether was typically used because it provided the cleanest reaction mixtures.
  • 14
    • 0042793055 scopus 로고    scopus 로고
    • note
    • 4 were also found to give extremely low levels of stereochemical induction.
  • 15
    • 0042793057 scopus 로고    scopus 로고
    • note
    • This observation has also been noted in the addition of enolsilanes to β-alkoxyaldehydes. See ref 3.
  • 17
    • 0042793056 scopus 로고    scopus 로고
    • note
    • The optimal solvent for these reactions is diethyl ether. However, the reaction mixture is heterogeneous from the point of enolization until the quench.
  • 21
    • 0042292100 scopus 로고    scopus 로고
    • note
    • This reaction has been carried out by Dr. Kenneth J. McRae (Harvard University).
  • 28
    • 0035826336 scopus 로고    scopus 로고
    • (a) Kozmin, S. A. Org. Lett. 2001, 3, 755-758. Wang, Y.; Janjic, J.; Kozmin, S. A. J. Am. Chem. Soc. 2002, 124, 13670-13671.
    • (2001) Org. Lett. , vol.3 , pp. 755-758
    • Kozmin, S.A.1
  • 29
  • 36
    • 0042793050 scopus 로고    scopus 로고
    • note
    • In the aldol reaction reported by Panek (eq 23), the indicated configurations of the acetal centers in both reactant and product are currently in question. This reaction has been reinvestigated by Professor L. C. Dias (Universidade Estadual de Campinas, Instituto De Quimica-UNICAMP, Caixa Postal 6154 Campinas SPBRAZIL) who has kindly informed me of his results and of the indicated configuration reassignment.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.