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Volumn 35, Issue 20, 1996, Pages 2363-2365

Catalytic, enantioselective addition of allylsilanes to aldehydes: Generation of a novel, reactive TiIV complex from TiF4

Author keywords

Allylations; Allylsilanes; Asymmetric catalysis; Synthetic methods; Titanium compounds

Indexed keywords


EID: 0030472831     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199623631     Document Type: Article
Times cited : (200)

References (41)
  • 3
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    • Ed.: C. H. Heathcock, Pergamon, Oxford
    • c) W. R. Roush in Comprehensive Organic Synthesis, Vol. 2 (Ed.: C. H. Heathcock), Pergamon, Oxford, 1990, pp. 1-53;
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    • Roush, W.R.1
  • 4
    • 0001525348 scopus 로고
    • d) R. W. Hoffman, Angew. Chem. 1982, 94, 569; Angew. Chem. Int. Ed. Engl. 1982, 21, 555;
    • (1982) Angew. Chem. , vol.94 , pp. 569
    • Hoffman, R.W.1
  • 5
    • 0020173674 scopus 로고
    • d) R. W. Hoffman, Angew. Chem. 1982, 94, 569; Angew. Chem. Int. Ed. Engl. 1982, 21, 555;
    • (1982) Angew. Chem. Int. Ed. Engl. , vol.21 , pp. 555
  • 6
    • 0041370973 scopus 로고
    • Applications of Allylboronates in the Synthesis of Carbohydrates and Polyhydroxylated Natural Products (Eds.: D. Horton, L. D. Hawkins, G. J. McGarvey), American Chemical Society, Washington, DC
    • e) W. R. Roush in Applications of Allylboronates in the Synthesis of Carbohydrates and Polyhydroxylated Natural Products (Eds.: D. Horton, L. D. Hawkins, G. J. McGarvey), ACS Symp. Ser. 386, American Chemical Society, Washington, DC, 1989, pp. 242-277.
    • (1989) ACS Symp. Ser. , vol.386 , pp. 242-277
    • Roush, W.R.1
  • 10
    • 33745161024 scopus 로고
    • c) B. Schmidt, D. Seebach, Angew. Chem. 1991, 103, 100; Angew. Chem. Int. Ed. Engl. 1991, 30, 99;
    • (1991) Angew. Chem. Int. Ed. Engl. , vol.30 , pp. 99
  • 23
    • 0001323711 scopus 로고
    • Iv complexes and their use in additions to aldehydes, see: a) R. O. Duthaler, A. Hafner, Chem. Rev. 1992, 92, 807;
    • (1992) Chem. Rev. , vol.92 , pp. 807
    • Duthaler, R.O.1    Hafner, A.2
  • 26
    • 0001483135 scopus 로고
    • H. Mayr, M. Patz, Angew. Chem. 199-4, 106, 990; Angew. Chem. Int. Ed. Engl. 1994, 33, 938.
    • (1994) Angew. Chem. , vol.106 , pp. 990
    • Mayr, H.1    Patz, M.2
  • 27
    • 33749141140 scopus 로고
    • H. Mayr, M. Patz, Angew. Chem. 199-4, 106, 990; Angew. Chem. Int. Ed. Engl. 1994, 33, 938.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 938
  • 31
    • 85033007035 scopus 로고    scopus 로고
    • note
    • The silyl-protected adducts are the predominant product in all of the addition reactions. Small amounts of the free alcohol products could also be isolated albeit in 5-10% yields. The % ee value of the alcohol product was found to be equal to that of the silyl-protected adduct for each of the aldehydes examined.
  • 32
    • 85032998694 scopus 로고    scopus 로고
    • note
    • 2 solution works well in the addition reaction and obviates the need to remove the bulk acetonitrile solvent.
  • 41
    • 25044437694 scopus 로고
    • Eds.: K. H. Dötz, R. W. Hoffman, Vieweg, Braunschweig
    • For an extensive discussion of the structure and spectroscopy of a well-defined chiral allyltitanium complex, see: R. O. Duthaler, A Hafner, M. Riediker In Organic Synthesis via Organometallics, (Eds.: K. H. Dötz, R. W. Hoffman), Vieweg, Braunschweig, 1991, p 285.
    • (1991) Organic Synthesis Via Organometallics , pp. 285
    • Duthaler, R.O.1    Hafner, A.2    Riediker, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.