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Volumn 12, Issue 9, 2006, Pages 2593-2606

[1,3]-Transfer of chirality during the nicholas reaction in γ-benzyloxy propargylic alcohols

Author keywords

Asymmetric synthesis; Cobalt; Natural products; Nicholas reaction; Propargylic alcohols

Indexed keywords

CARBON; COBALT; ETHERS; SYNTHESIS (CHEMICAL);

EID: 33644894735     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200501127     Document Type: Article
Times cited : (13)

References (62)
  • 3
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    • (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, New York
    • a) Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, New York, 1999;
    • (1999) Comprehensive Asymmetric Catalysis
  • 4
    • 0003905731 scopus 로고
    • (Ed.: J. D. Morrison), Academic Press
    • b) Asymmetric Synthesis (Ed.: J. D. Morrison), Academic Press, 1985.
    • (1985) Asymmetric Synthesis
  • 5
    • 33644915758 scopus 로고    scopus 로고
    • note
    • From a rigorous chemical point of view, the term "chirality transfer" relates to asymmetric induction whereby one stereogenic element is sacrificed and another is created. However, its use has also been widely extended to processes in which the original asymmetric center remains intact during the chirality transfer.
  • 16
    • 18844395162 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 2756-2760.
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 2756-2760
  • 32
    • 33644907120 scopus 로고    scopus 로고
    • 2) were used
    • 2) were used.
  • 37
    • 33644881326 scopus 로고    scopus 로고
    • Benzaldehyde was detected and characterized as a resulting byproduct
    • Benzaldehyde was detected and characterized as a resulting byproduct.
  • 38
    • 33644896173 scopus 로고    scopus 로고
    • For the preparation of 8, see the Experimental Section
    • For the preparation of 8, see the Experimental Section.
  • 39
    • 33644905228 scopus 로고    scopus 로고
    • For the stereochemical assignment of the newly created stereocenter, see below
    • For the stereochemical assignment of the newly created stereocenter, see below.
  • 40
    • 0003942864 scopus 로고
    • Wiley, New York
    • The relationship between bulkiness of the group and selectivity is roughly in agreement with the relative conformational free-energy values for such substituents on cyclohexanes, see: E. L. Eliel, S. H. Eliel, L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1993, pp. 696-697.
    • (1993) Stereochemistry of Organic Compounds , pp. 696-697
    • Eliel, E.L.1    Eliel, S.H.2    Mander, L.N.3
  • 43
    • 33644924559 scopus 로고
    • (Ed.: J. D. Morrison), Academic Press, New York, and references therein
    • D. A. Evans, Asymmetric Synthesis, Vol. 4 (Ed.: J. D. Morrison), Academic Press, New York, 1985, pp. 2110, and references therein.
    • (1985) Asymmetric Synthesis , vol.4 , pp. 2110
    • Evans, D.A.1
  • 51
    • 33845555760 scopus 로고
    • To describe the relative stereochemistry in the linear chains, we applied the criteria discussed in: S. Masamune, T. Kaiho, D. S. Garvey, J. Am. Chem. Soc. 1982, 104, 5521-5523.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 5521-5523
    • Masamune, S.1    Kaiho, T.2    Garvey, D.S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.