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Volumn , Issue 12, 2005, Pages 1917-1921

Metal chloride-promoted aldol reaction of α-dimethylsilylesters with aldehydes, ketones, and α-enones

Author keywords

silylesters; Aldehydes; Aldol reactions; Ketones; Michael additions

Indexed keywords

ALDEHYDE; ALPHA DIMETHYLSILYL ESTER; ALPHA ENONE; CHLORIDE; ESTER DERIVATIVE; KETONE; LITHIUM CHLORIDE; MAGNESIUM CHLORIDE; UNCLASSIFIED DRUG;

EID: 23644438866     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-871938     Document Type: Article
Times cited : (13)

References (46)
  • 1
    • 11844259698 scopus 로고    scopus 로고
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    • (a) Modern Aldol Reactions, Vol. 2; Mahrwald, R., Ed.; Wiley-VCH: Weinheim Germany, 2004.
    • (2004) Modern Aldol Reactions , vol.2
    • Mahrwald, R.1
  • 2
    • 10044241080 scopus 로고    scopus 로고
    • Yamamoto, H.; Oshima, K., Eds.; Wiley-VCH: Weinheim Germany, Chap. 10
    • (b) Miura, K.; Hosomi, A. In Main Group Metals in Organic Synthesis, Vol. 2; Yamamoto, H.; Oshima, K., Eds.; Wiley-VCH: Weinheim Germany, 2004, Chap. 10, 409.
    • (2004) Main Group Metals in Organic Synthesis , vol.2 , pp. 409
    • Miura, K.1    Hosomi, A.2
  • 3
    • 0001316868 scopus 로고
    • Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, Chap. 2.4
    • (c) Gennari, C. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Chap. 2.4, 629.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 629
    • Gennari, C.1
  • 22
    • 33645171384 scopus 로고    scopus 로고
    • note
    • 2Si (%): C, 49.53; H, 9.69. Found: C, 49.27; H, 9.65.
  • 23
    • 33645180464 scopus 로고    scopus 로고
    • note
    • 4 and evaporated. The crude product was purified by silica gel column chromatography.
  • 24
    • 1542497521 scopus 로고
    • The Reformatsky reaction of ethyl bromoacetate with 5g shows much lower stereoselectivity toward equatorial attack. See: (a) Screttas, C. G.; Smonou, I. C. J. Org. Chem. 1988, 53, 893.
    • (1988) J. Org. Chem. , vol.53 , pp. 893
    • Screttas, C.G.1    Smonou, I.C.2
  • 35
    • 0001383034 scopus 로고
    • Lewis base catalyzed reactions: (a) RajanBabu, T. V. J. Org. Chem. 1984, 49, 2083.
    • (1984) J. Org. Chem. , vol.49 , pp. 2083
    • RajanBabu, T.V.1
  • 45
    • 0001019927 scopus 로고
    • Patai, S.; Rappoport, Z., Eds.; Wiley: Chichester UK, Chap. 5
    • 3SiBr (402 kJ/mol). See: Walsh, R. In The Chemistry of Organic Silicon Compounds, Vol. 1; Patai, S.; Rappoport, Z., Eds.; Wiley: Chichester UK, 1989, Chap. 5, 371.
    • (1989) The Chemistry of Organic Silicon Compounds , vol.1 , pp. 371
    • Walsh, R.1
  • 46
    • 33645187616 scopus 로고    scopus 로고
    • note
    • As shown in Table 3, the reaction of 1a with 8a proceeded efficiently irrespective of the metal chloride used. This observation may be due to higher coordinating ability (Lewis basicity) of α-enones, which allows carbonyl activation even with less Lewis acidic metal ions. For the coordinating ability of α-enones, see ref. 17a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.