메뉴 건너뛰기




Volumn 4, Issue 16, 2006, Pages 3048-3051

A diastereoselective and concise synthesis of functionalised vinyl epoxides with a Morita-Baylis-Hillman backbone

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CATALYSIS; REACTION KINETICS; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

EID: 33746862174     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b607040j     Document Type: Article
Times cited : (21)

References (61)
  • 8
    • 33750456293 scopus 로고
    • B. M. Trost, I. Fleming and L. A. Paquette, Pergamon Press, New York, p. 899; for a recent selected example, see:
    • For a review, see: T. Hudlicky and J. W. Reed, in Comprehensive Organic Synthesis, vol. 5, ed., B. M. Trost, I. Fleming, and, L. A. Paquette, Pergamon Press, New York, 1991, p. 899
    • (1991) Comprehensive Organic Synthesis, Vol. 5, Ed.
    • Hudlicky, T.1    Reed In, J.W.2
  • 13
    • 0037195680 scopus 로고    scopus 로고
    • (a recent example) via the asymmetric dihydroxylation of alkenes, see:
    • B. Olofsson P. Somfai J. Org. Chem. 2002 67 8574
    • (2002) J. Org. Chem. , vol.67 , pp. 8574
    • Olofsson, B.1    Somfai, P.2
  • 15
    • 0003445429 scopus 로고    scopus 로고
    • E. N. Jacobson, A. Pfaltz and H. Yamamoto, Springer-Verlag, Berlin, p. 713 for the direct asymmetric epoxidation of conjugated dienes:
    • I. E. Markó and J. S. Svendsen, in Comprehensive Asymmetric Catalysis, vol. 2, ed., E. N. Jacobson, A. Pfaltz, and, H. Yamamoto, Springer-Verlag, Berlin, 1999, p. 713
    • (1999) Comprehensive Asymmetric Catalysis, Vol. 2, Ed.
    • Markó, I.E.1    Svendsen In, J.S.2
  • 22
    • 4143093678 scopus 로고    scopus 로고
    • For ylide epoxidation starting from the pre-formed allylic sulfonium salt, see:
    • V. K. Aggarwal C. L. Winn Acc. Chem. Res. 2004 37 611
    • (2004) Acc. Chem. Res. , vol.37 , pp. 611
    • Aggarwal, V.K.1    Winn, C.L.2
  • 27
    • 0033537059 scopus 로고    scopus 로고
    • For the alternative asymmetric synthesis of vinyl epoxides from addition of sulfonium ylide reagents to α,β-unsaturated aldehydes, see:
    • A. Fürstner O. Guth A. Rumbo G. Seidel J. Am. Chem. Soc. 1999 121 11108
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 11108
    • Fürstner, A.1    Guth, O.2    Rumbo, A.3    Seidel, G.4
  • 29
    • 33746909702 scopus 로고    scopus 로고
    • see also ref. 113a and 14a
    • see also ref. 113a and 14a
  • 33
    • 33746921846 scopus 로고    scopus 로고
    • see also ref. 10a for other rearrangement events; (e) see ref. 12 and 13 for further discussions
    • see also ref. 10a for other rearrangement events; (e) see ref. 12 and 13 for further discussions.
  • 36
    • 0042066450 scopus 로고    scopus 로고
    • For an alternative asymmetric procedure making use of the pre-formation of the allylic sulfonium salt, see:
    • K. Li X.-M. Deng Y. Tang Chem. Commun. 2003 2074
    • (2003) Chem. Commun. , pp. 2074
    • Li, K.1    Deng, X.-M.2    Tang, Y.3
  • 43
    • 0002793868 scopus 로고
    • and references cited therein To the best of our knowledge, this is the only precedent which supposes the in situ formation of these kind of epoxides (with a carboxylic acrylic acid moiety) from the addition of a sulfonium ylide to aldehydes. Unfortunately, this elegant process is poorly diastereoselective and cannot be catalytic in sulfide, see:
    • K. Tanaka H. Horiuchi H. Yoda J. Org. Chem. 1989 54 63
    • (1989) J. Org. Chem. , vol.54 , pp. 63
    • Tanaka, K.1    Horiuchi, H.2    Yoda, H.3
  • 51
    • 0026518702 scopus 로고
    • During this work, an elegant allylidenation of tosylimines to aziridines was described with 2-(bromomethyl)acrylate derivatives. However, these acrylates are β-functionalised with a phenyl group with could have an extra stabilisation effect of the alkene moiety:
    • S. Nampalli R. S. Bhide H. Nakai Synth. Commun. 1992 22 1165
    • (1992) Synth. Commun. , vol.22 , pp. 1165
    • Nampalli, S.1    Bhide, R.S.2    Nakai, H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.