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Volumn 42, Issue 8, 2003, Pages 941-943

Asymmetric epoxidation of homoallylic alcohols and application in a concise total synthesis of (-)-α-bisabolol and (-)-8-epi-α-bisabolol

Author keywords

Bisabolol; Epoxidation; Homoallylic alcohols; Hydroxamic acids; Vanadium

Indexed keywords

AMINO ACIDS; CATALYSTS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); VANADIUM COMPOUNDS;

EID: 0037463034     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390250     Document Type: Article
Times cited : (71)

References (34)
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    • For selected recent reviews of the asymmetric epoxidation of functionalized alkenes, see: a) R. A. Johnson, K. B. Sharpless in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley-VCH, New York, 2000, p. 231; b) T. Katsuki in Comprehensive Asymmetric Catalysis I-III, Vol. 2 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, p. 621; c) T. Katsuki, V. S. Martin, Org. React. 1996, 48, 1.
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    • For selected reviews of the asymmetric epoxidation of unfunctionalized alkenes, see: a) V. Schurig, F. Betschinger, Chem. Rev. 1992, 92, 873; b) K. A. Jörgensen, Chem. Rev. 1989, 89, 431; c) T. Katsuki in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley-VCH, New York, 2000, p. 287; d) E. N. Jacobsen, M. H. Wu in Comprehensive Asymmetric Catalysis I-III, Vol. 2 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, p. 649.
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    • For selected reviews of the asymmetric epoxidation of unfunctionalized alkenes, see: a) V. Schurig, F. Betschinger, Chem. Rev. 1992, 92, 873; b) K. A. Jörgensen, Chem. Rev. 1989, 89, 431; c) T. Katsuki in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley-VCH, New York, 2000, p. 287; d) E. N. Jacobsen, M. H. Wu in Comprehensive Asymmetric Catalysis I-III, Vol. 2 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, p. 649.
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    • For selected reviews of the asymmetric epoxidation of unfunctionalized alkenes, see: a) V. Schurig, F. Betschinger, Chem. Rev. 1992, 92, 873; b) K. A. Jörgensen, Chem. Rev. 1989, 89, 431; c) T. Katsuki in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley-VCH, New York, 2000, p. 287; d) E. N. Jacobsen, M. H. Wu in Comprehensive Asymmetric Catalysis I-III, Vol. 2 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, p. 649.
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    • For selected reviews of the asymmetric epoxidation of unfunctionalized alkenes, see: a) V. Schurig, F. Betschinger, Chem. Rev. 1992, 92, 873; b) K. A. Jörgensen, Chem. Rev. 1989, 89, 431; c) T. Katsuki in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley-VCH, New York, 2000, p. 287; d) E. N. Jacobsen, M. H. Wu in Comprehensive Asymmetric Catalysis I-III, Vol. 2 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, p. 649.
    • (1999) Comprehensive Asymmetric Catalysis I-III, Vol. 2 , vol.2 , pp. 649
    • Jacobsen, E.N.1    Wu, M.H.2
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    • The asymmetric epoxidation of allylic alcohols using vanadium and an optically active hydroxamic acid was first reported by K. B. Sharpless in 1977: R. C. Michaelson, R. E. Palermo, K. B. Sharpless, J. Am. Chem. Soc. 1977, 99, 1990.
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  • 22
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    • note
    • [5b]
  • 24
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    • note
    • 2AlCl and formaldehyde according to ref. [14a].
  • 33
    • 0242560453 scopus 로고    scopus 로고
    • note
    • 3, 25°C TMS): δ=133.9, 131.3, 124.6, 120.6, 74.1, 42.9, 40.1, 31.0, 26.9, 25.6, 23.3, 23.2, 23.0, 22.0, 17.6 ppm.
  • 34
    • 0242476719 scopus 로고    scopus 로고
    • note
    • 3, 25°C, TMS): δ=133.9, 131.8, 124.7, 120.9, 74.4, 43.4, 39.4, 31.1, 26.2, 25.8, 24.1, 24.0, 23.5, 22.4, 17.8 ppm.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.