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Volumn 70, Issue 25, 2005, Pages 10584-10587

Generation of acyl anion equivalents from acylphosphonates via phosphonate - phosphate rearrangement: A highly practical method for cross-benzoin reaction

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; KETONES; NEGATIVE IONS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 28744457017     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051811u     Document Type: Article
Times cited : (86)

References (35)
  • 20
    • 1542375011 scopus 로고    scopus 로고
    • Stetter reaction with acylsilanes. For organocatalysis, see: (a) Mattson, A. E.; Bharadwaj, A. R.; Scheidt, K. A. J. Am. Chem. Soc. 2004, 126, 2314-2315. For metallophosphite catalysis, see:
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 2314-2315
    • Mattson, A.E.1    Bharadwaj, A.R.2    Scheidt, K.A.3
  • 24
    • 0035835953 scopus 로고    scopus 로고
    • (b) Moser, W. H. Tetrahedron 2001, 57, 2065-2084 and references therein.
    • (2001) Tetrahedron , vol.57 , pp. 2065-2084
    • Moser, W.H.1
  • 28
    • 0029084326 scopus 로고
    • (c) Ruel, R.; Bouvier, J.-P.; Young, R. N. J. Org. Chem. 1995, 60, 5209-5213. Cyanide anion promoted phosphonate-phosphate rearrangement of acetylphosphonate in aqueous medium was reported; see:
    • (1995) J. Org. Chem. , vol.60 , pp. 5209-5213
    • Ruel, R.1    Bouvier, J.-P.2    Young, R.N.3
  • 31
    • 0342887750 scopus 로고
    • For examples of stoichiometric generation of acyl anion equivalents from α-cyanophosphates and their reactions, see: (a) Kurihara, T.; Santo, K.; Harusawa, S.; Yoneda, R.; Chem. Pharm. Bull. 1987, 35, 4777-4788.
    • (1987) Chem. Pharm. Bull. , vol.35 , pp. 4777-4788
    • Kurihara, T.1    Santo, K.2    Harusawa, S.3    Yoneda, R.4
  • 33
    • 28744437179 scopus 로고    scopus 로고
    • note
    • This mechanistic picture is based on the well-known benzoin reaction mechanism and its congeners; see refs 1, 4, and 9.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.