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Volumn 126, Issue 8, 2004, Pages 2314-2315

The Thiazolium-Catalyzed Sila-Stetter Reaction: Conjugate Addition of Acylsilanes to Unsaturated Esters and Ketones

Author keywords

[No Author keywords available]

Indexed keywords

ACYLSILANE DERIVATIVE; ESTER DERIVATIVE; KETONE DERIVATIVE; SILANE DERIVATIVE; THIAZOLE DERIVATIVE; THIAZOLIUM; UNCLASSIFIED DRUG;

EID: 1542375011     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0318380     Document Type: Article
Times cited : (206)

References (29)
  • 6
    • 0007235441 scopus 로고
    • Paquette, L. A., Ed.; Wiley and Sons: New York
    • Stetter, H.; Kuhlmann, H. In Organic Reactions; Paquette, L. A., Ed.; Wiley and Sons: New York, 1991; Vol. 40.
    • (1991) Organic Reactions , vol.40
    • Stetter, H.1    Kuhlmann, H.2
  • 9
    • 0018422536 scopus 로고
    • Tethering the aldehyde to the conjugate acceptor (intramolecular reaction) or significant excess of aldehyde can alleviate the problem of benzoin formation in the Stetter reaction, see: (a) Trost, B. M.; Shuey, C. D.; Dininno, F.; McElvain, S. S. J. Am. Chem. Soc. 1979, 101, 1284-1285.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 1284-1285
    • Trost, B.M.1    Shuey, C.D.2    Dininno, F.3    McElvain, S.S.4
  • 14
  • 21
    • 0002237394 scopus 로고
    • and references therein
    • (a) Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84 and references therein.
    • (1974) Acc. Chem. Res. , vol.7 , pp. 77-84
    • Brook, A.G.1
  • 22
    • 0035835953 scopus 로고    scopus 로고
    • (b) Moser, W. H. Tetrahedron 2001, 57, 2065-2084.
    • (2001) Tetrahedron , vol.57 , pp. 2065-2084
    • Moser, W.H.1
  • 23
    • 1542349851 scopus 로고    scopus 로고
    • note
    • Control experiments omitting either DBU (1,8-diazoabicyclo-[5.4.0]-undecane) or 4 resulted in no product formation.
  • 24
    • 1542349852 scopus 로고    scopus 로고
    • note
    • Thiazolium salts such as 3-benzyl-4,5-dimethylthiazolium bromide afford no product when exogenous alcohols were omitted from the reaction.
  • 25
    • 1542379644 scopus 로고    scopus 로고
    • note
    • The use of benzoyltrimethylsilane (1a) for these reactions results in significantly reduced conversion. This observation is under investigation.
  • 26
    • 0030569373 scopus 로고    scopus 로고
    • For mechanistic investigations of thiazolium salts as catalysts, see: (a) Breslow, R.; Schmuck, C. Tetrahedron Lett. 1996, 37, 8241-8242.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 8241-8242
    • Breslow, R.1    Schmuck, C.2
  • 28
    • 1542349853 scopus 로고    scopus 로고
    • note
    • The use of 3-octanol in the reaction affords 3-trimethylsilyloxyoctane (observed by gas chromatography), thus implicating the alcohol as the ultimate silyl acceptor. See Supporting Information for details.
  • 29
    • 1542319803 scopus 로고    scopus 로고
    • note
    • Replacing la with PhCHO affords mainly benzoin and only 20-30% of 5.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.