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Volumn 40, Issue 22, 1999, Pages 4227-4230

Catalytic TMSCl promoted powerful aldol addition and Claisen condensation mediated by TiCl4/Bu3N agent: Comparison and evaluation with the Mukaiyama aldol addition

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ESTER DERIVATIVE; KETONE DERIVATIVE; TITANIUM DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

EID: 0033612353     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00682-6     Document Type: Article
Times cited : (51)

References (34)
  • 12
    • 33847804804 scopus 로고
    • a) Mukaiyama, T.; Banno, K.; Narasaka, K. Chem. Lett. 1973, 1011; J. Am. Chem. Soc. 1974, 96, 7503.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 7503
  • 13
    • 0000145196 scopus 로고
    • Wiley: New York
    • b) Mukaiyama, T. Organic Reactions; Wiley: New York, 1982; Vol. 28, p. 203.
    • (1982) Organic Reactions , vol.28 , pp. 203
    • Mukaiyama, T.1
  • 14
    • 0000487061 scopus 로고
    • Trost, B. M.; Fleming I. Eds.; Pergamon: Oxford
    • c) Heathcock, C. H. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming I. Eds.; Pergamon: Oxford, 1991; Vol. 2, p. 181.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 181
    • Heathcock, C.H.1
  • 15
    • 0003905731 scopus 로고
    • Morrison, J. D., Ed; Academic Press: New York
    • d) Heathcock, C. H. In Asymmetric Synthesis, Morrison, J. D., Ed; Academic Press: New York, 1984, p. 111.
    • (1984) Asymmetric Synthesis , pp. 111
    • Heathcock, C.H.1
  • 21
    • 0013572146 scopus 로고    scopus 로고
    • note
    • The reaction mode of the present method resembles that of trichlorotitanium enolate reaction (C) rather than the original Mukaiyama aldol addition (B), judging from the stereochemical results of cyclohexanone with benzaldehyde (79%; syn : anti = 95:5).
  • 26
  • 27
    • 0027960686 scopus 로고
    • note
    • 1H NMR (400 MHz) [syn-isomer] δ 0.21 (9H, s), 5.22 (1H, d, J = 8.0 Hz), 5.26 (1H, d, J = 8.0 Hz), 7.22-7.99 (10H, m); [anti-isomer] δ -0.15 (9H, s), 5.08 (1H, d, J = 9.2 Hz), 5.16 (1H, d, J = 9.2 Hz), 7.22-7.99 (10H, m).
    • (1994) Tetrahedron Lett. , vol.35 , pp. 8409
    • Tanabe, Y.1    Murakami, M.2    Kitaichi, K.3    Yoshida, Y.4
  • 28
    • 0013570220 scopus 로고    scopus 로고
    • note
    • 2 at-78 °C showed progressive appearance of enol carbon peak (δ 135.85 and 151.20) of the titanium enolate.
  • 33
    • 0013569545 scopus 로고    scopus 로고
    • note
    • 2 column chromatography (hexane-AcOEt = 8:1) gave methyl 2-benzyl-3-oxo-3-phenylpropionate (216 mg, 81%).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.