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Volumn 73, Issue 20, 2008, Pages 7990-7995

Enantiopure quaternary α-trifluoromethyl-α-alkoxyaldehydes from L-tartaric acid derived ketoamides

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; ORGANIC COMPOUNDS;

EID: 53849129962     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8013403     Document Type: Article
Times cited : (22)

References (68)
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    • For reviews on nucleophilic trifluoromethylation, see: a
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  • 21
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    • 3, etc. have also been described but with low yields; see: Hagiwara, T.; Kobayashi, T.; Fuchikami, T. Main Group Chem. 1997, 2, 13-15.
    • 3, etc. have also been described but with low yields; see: Hagiwara, T.; Kobayashi, T.; Fuchikami, T. Main Group Chem. 1997, 2, 13-15.
  • 46
    • 37549027127 scopus 로고    scopus 로고
    • For examples of total synthesis of natural products from tartaric acid derived ketoamides, see: Prasad, K. R, Gholap, S. L. J. Org. Chem. 2008, 73, 2-11, and references therein
    • For examples of total synthesis of natural products from tartaric acid derived ketoamides, see: Prasad, K. R.; Gholap, S. L. J. Org. Chem. 2008, 73, 2-11, and references therein.
  • 52
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  • 53
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    • 3 in the presence of a catalytic amount of fluoride gave the corresponding hemiaminal: Monnier-Benoit, N.; Massicot, F.; Portella, C. unpublished results. (Chemical Equation Presented)
    • 3 in the presence of a catalytic amount of fluoride gave the corresponding hemiaminal: Monnier-Benoit, N.; Massicot, F.; Portella, C. unpublished results. (Chemical Equation Presented)
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    • 2O, see: Christe, K. O.; Wilson, W. W.; Wilson, R. D.; Bau, R.; Feng, J. J. Am. Chem. Soc. 1990, 112, 7619-7625.
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    • For various methodologies for converting silyl ethers into alkyl ethers, see: a
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    • (1969) Tetrahedron Lett , vol.48 , pp. 4225-4228
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    • A procedure similar to the one reported in the Experimental Section for the millimolar scale was applied, except for the purification of the ketoamide 5 and the intermediate (R)-13, which was carried out by crystallization instead of flash chromatography (crystallization solvents were petroleum ether/Et2O for 5, petroleum ether for (R)-13
    • 2O for 5, petroleum ether for (R)-13).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.