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Volumn 128, Issue 49, 2006, Pages 15632-15636

Tandem enyne metathesis and Claisen rearrangement: A versatile approach to conjugated dienes of variable substitution patterns

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; SUBSTITUTION REACTIONS;

EID: 33845448137     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja063132m     Document Type: Article
Times cited : (42)

References (57)
  • 1
    • 0004198491 scopus 로고
    • Wiley: New York
    • General reviews on tandem reactions: (a) Ho, T. L. Tandem Organic Reactions; Wiley: New York, 1992.
    • (1992) Tandem Organic Reactions
    • Ho, T.L.1
  • 3
    • 0028879573 scopus 로고
    • (c) Bunce, R. A. Tetrahedron 1995, 51, 13103-13159.
    • (1995) Tetrahedron , vol.51 , pp. 13103-13159
    • Bunce, R.A.1
  • 13
  • 17
    • 33845278565 scopus 로고
    • The Ireland-Claisen has been used to transform nonconjugated dienes to conjugated dienes. see: (a) Wender, P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 5904-5906
    • Wender, P.A.1    Ihle, N.C.2    Correia, C.R.D.3
  • 31
    • 0142169492 scopus 로고    scopus 로고
    • For an excellent discussion of the regiochemistry of nitroso ene reactions, see: Adam, W.; Krebs, O. Chem. Rev. 2003, 103, 4131-4146.
    • (2003) Chem. Rev. , vol.103 , pp. 4131-4146
    • Adam, W.1    Krebs, O.2
  • 33
  • 41
    • 33845394095 scopus 로고    scopus 로고
    • note
    • See Supporting Information for details.
  • 45
    • 33845441007 scopus 로고    scopus 로고
    • note
    • In these stereochemical descriptors, the asterisk denotes the known chirality from the Mosher ester.
  • 47
    • 33845413112 scopus 로고    scopus 로고
    • note
    • In the few instances where the Mosher method is unsuccessful (see ref 14), poor separation (Δδ = 0.00-0.05 ppm) in both diastereomers was observed. In the case of 23A,B, this was not the case as there was found to be greater chemical shift dispersion in one diastereomeric Mosher ester (expected range is Δδ = 0.14-0.20 ppm) and almost none in the other.
  • 57
    • 33845453533 scopus 로고    scopus 로고
    • note
    • 3 under heating for a 2 h period.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.