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Volumn 49, Issue 7, 2008, Pages 1169-1174

Stereoselective synthesis of chiral tertiary alcohol building blocks via neighbouring group participation from tri-substituted olefins

Author keywords

Chiral quaternary 1,2 1,3 diols; Sulfoxide; Tri substituted alkenes

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE DERIVATIVE;

EID: 38349076159     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.12.046     Document Type: Article
Times cited : (12)

References (82)
  • 5
    • 38349066344 scopus 로고    scopus 로고
    • note
    • Representative examples of tertiary carbinol containing bioactive compounds: Cinatrin C, Integerrimine, Harringtonine, K-252-a, Fostriecin, Viridofungin, Erythromycin and Zaragozic acid.
  • 6
    • 0001403071 scopus 로고    scopus 로고
    • Asymmertic epoxidation:. Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds), Springer, Heidelberg Chapter 18.1
    • Asymmertic epoxidation:. Katsuki T. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vol. 2 (1999), Springer, Heidelberg Chapter 18.1
    • (1999) Comprehensive Asymmetric Catalysis , vol.2
    • Katsuki, T.1
  • 7
    • 0000345527 scopus 로고    scopus 로고
    • Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds), Springer, Heidelberg Chapter 18.2
    • Jacobsen E.N., and Wu M.F. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vol. 2 (1999), Springer, Heidelberg Chapter 18.2
    • (1999) Comprehensive Asymmetric Catalysis , vol.2
    • Jacobsen, E.N.1    Wu, M.F.2
  • 9
    • 0003445429 scopus 로고    scopus 로고
    • Asymmetric hydroxylation:. Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds), Springer, Heidelberg Chapter 20
    • Asymmetric hydroxylation:. Marko I.E., and Svensen J.S. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vol. 2 (1999), Springer, Heidelberg Chapter 20
    • (1999) Comprehensive Asymmetric Catalysis , vol.2
    • Marko, I.E.1    Svensen, J.S.2
  • 28
    • 0344994587 scopus 로고    scopus 로고
    • For the oxidative functionalization of di-substituted alkenes refer:
    • For the oxidative functionalization of di-substituted alkenes refer:. Raghavan S., Rasheed M.A., Joseph S.C., and Rajender A. Chem. Commun. (1999) 1845
    • (1999) Chem. Commun. , pp. 1845
    • Raghavan, S.1    Rasheed, M.A.2    Joseph, S.C.3    Rajender, A.4
  • 29
    • 0037999777 scopus 로고    scopus 로고
    • For the application of this methodology in the synthesis of bioactive target molecules refer:
    • For the application of this methodology in the synthesis of bioactive target molecules refer:. Raghavan S., and Ramakrishna Reddy S. J. Org. Chem. 68 (2003) 5754
    • (2003) J. Org. Chem. , vol.68 , pp. 5754
    • Raghavan, S.1    Ramakrishna Reddy, S.2
  • 41
    • 0034719257 scopus 로고    scopus 로고
    • The unsaturated aldehydes were obtained from the corresponding esters in two steps, (a) reduction using DIBAL-H to furnish the allyl alcohols followed by (b) oxidation using Swern protocol. The esters themselves were prepared using procedures reported in the literature, ester corresponding to 2, refer:
    • The unsaturated aldehydes were obtained from the corresponding esters in two steps, (a) reduction using DIBAL-H to furnish the allyl alcohols followed by (b) oxidation using Swern protocol. The esters themselves were prepared using procedures reported in the literature, ester corresponding to 2, refer:. Koppisch A.T., Blagg B.S.J., and Poulter C.D. Org. Lett. 2 (2000) 215
    • (2000) Org. Lett. , vol.2 , pp. 215
    • Koppisch, A.T.1    Blagg, B.S.J.2    Poulter, C.D.3
  • 42
    • 0344961695 scopus 로고    scopus 로고
    • For ester corresponding to 3 refer:
    • For ester corresponding to 3 refer:. Baldwin I.R., and Whitby R.J. Chem. Commun. (2003) 2786
    • (2003) Chem. Commun. , pp. 2786
    • Baldwin, I.R.1    Whitby, R.J.2
  • 45
    • 0001296747 scopus 로고
    • The configuration of anti- and syn-isomers were assigned by comparison of coupling constants for the methylene protons directly bonded to the carbon of the β-hydroxy sulfoxide moiety and the chemical shift of the β-methine proton. Refer: and references cited therein
    • The configuration of anti- and syn-isomers were assigned by comparison of coupling constants for the methylene protons directly bonded to the carbon of the β-hydroxy sulfoxide moiety and the chemical shift of the β-methine proton. Refer:. Carreno M.C., Garcia Ruano T.L., Martin A.M., Pedregal C., Rodrigues J.H., Rubio A., Sanchez J., and Solladie G. J. Org. Chem. 55 (1990) 2120 and references cited therein
    • (1990) J. Org. Chem. , vol.55 , pp. 2120
    • Carreno, M.C.1    Garcia Ruano, T.L.2    Martin, A.M.3    Pedregal, C.4    Rodrigues, J.H.5    Rubio, A.6    Sanchez, J.7    Solladie, G.8
  • 47
    • 0040454662 scopus 로고
    • For a modern interpretation, see:
    • For a modern interpretation, see:. Isenberg N., and Grdinic M. J. Chem. Educ. 46 (1969) 601
    • (1969) J. Chem. Educ. , vol.46 , pp. 601
    • Isenberg, N.1    Grdinic, M.2
  • 49
    • 38349071003 scopus 로고    scopus 로고
    • See Electronic Supplementary data.
  • 53
    • 0001071070 scopus 로고
    • Ref. 7l. Also refer: The positive optical rotation for the substrates and the negative rotation for the products also support inversion of sulfoxide configuration, refer: Electronic Supplementary data
    • Ref. 7l. Also refer:. Dalton D.R., Dutta V.P., and Jones D.C. J. Am. Chem. Soc. 90 (1968) 5498 The positive optical rotation for the substrates and the negative rotation for the products also support inversion of sulfoxide configuration, refer: Electronic Supplementary data
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 5498
    • Dalton, D.R.1    Dutta, V.P.2    Jones, D.C.3
  • 79
    • 38349072068 scopus 로고    scopus 로고
    • note
    • Compound 15 was obtained from 7s prepared in two steps (i. formation of β-keto sulfoxide and ii. stereoselective reduction of keto sulfoxide, 53% overall yield) as depicted {A figure is presented}.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.