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Volumn 128, Issue 25, 2006, Pages 8132-8133

Gold(I)-catalyzed synthesis of dihydropyrans

Author keywords

[No Author keywords available]

Indexed keywords

GOLD; PYRAN DERIVATIVE; VINYL DERIVATIVE;

EID: 33745677660     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja061344d     Document Type: Article
Times cited : (195)

References (55)
  • 3
    • 10044268769 scopus 로고    scopus 로고
    • For recent examples of pyran synthesis using tandem reactions, see the following. Oxonia Cope-Prins: (a) Dalgard, J. E.; Rychnovsky, S. D. J. Am. Chem. Soc. 2004, 126, 15662.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 15662
    • Dalgard, J.E.1    Rychnovsky, S.D.2
  • 10
    • 33845375114 scopus 로고
    • For reviews concerning tandem reactions, see: (a) Posner, G. H. Chem. Rev. 1986, 86, 831.
    • (1986) Chem. Rev. , vol.86 , pp. 831
    • Posner, G.H.1
  • 12
    • 0027999819 scopus 로고
    • (c) Hall, N. Science 1994, 266, 32.
    • (1994) Science , vol.266 , pp. 32
    • Hall, N.1
  • 20
    • 17744400103 scopus 로고    scopus 로고
    • For some recent examples of alkyne activation by Au(I) complexes, see: (a) Shi, X.; Gorin, D. J.; Toste F. D. J. Am. Chem. Soc. 2005, 127, 5802.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 5802
    • Shi, X.1    Gorin, D.J.2    Toste, F.D.3
  • 32
    • 28844458694 scopus 로고    scopus 로고
    • For allene activation by Au(I), see: (a) Zhang, L. J. Am. Chem. Soc. 2005, 127, 16804.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 16804
    • Zhang, L.1
  • 40
    • 22944485617 scopus 로고    scopus 로고
    • For reviews of additions to allenes, see: (i) Ma, S. Chem. Rev. 2005, 105, 2829.
    • (2005) Chem. Rev. , vol.105 , pp. 2829
    • Ma, S.1
  • 44
    • 33745667603 scopus 로고    scopus 로고
    • note
    • 2 gave only allenyl aldehyde 2 even the presence of water. THF and dioxane afforded the desired pyran in 14 and 4 h, respectively. Reactions in DME returned only starting material.
  • 45
    • 33745659060 scopus 로고    scopus 로고
    • note
    • 8aan unidentified aldehyde.
  • 46
    • 33745654615 scopus 로고    scopus 로고
    • note
    • Relative stereochemistry was ascertained through nOe analysis; see Supporting Information for details.
  • 47
    • 33745672604 scopus 로고    scopus 로고
    • note
    • The enantiomeric excess of pyran 6f was determined after in situ reduction to the corresponding allylic alcohol (see Supporting Information for details).
  • 54
    • 0037028560 scopus 로고    scopus 로고
    • An alternative mechanism in which gold(I) catalyzes the addition of the hemiacetal, not the aldehyde, to the allene is also possible. See: (a) Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 764
    • Asao, N.1    Nogami, T.2    Takahashi, K.3    Yamamoto, Y.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.