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Volumn 9, Issue 21, 1998, Pages 3731-3735

Stereocontrolled approaches to (+)- and (-)-γ-trifluoromethyl-GABOB, a new hydroxymethylene (statine) dipeptide isostere

Author keywords

[No Author keywords available]

Indexed keywords

DIPEPTIDE; GAMMA TRIFLUOROMETHYL GAMMA AMINO BETA HYDROXY BUTYRIC ACID; STATINE; UNCLASSIFIED DRUG;

EID: 0032491553     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00397-8     Document Type: Article
Times cited : (34)

References (43)
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    • and references cited therein
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    • Trifluoromethylated amino alcohols: New synthetic approaches and medicinal targets
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    • (a) Bégué, J.-P.; Bonnet-Delpon, D. Trifluoromethylated amino alcohols: new synthetic approaches and medicinal targets. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds; ACS Books, American Chemical Society: Washington, DC, 1996; pp. 59-72.
    • (1996) Biomedical Frontiers of Fluorine Chemistry , pp. 59-72
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  • 21
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    • note
    • (i) Attempts to improve the stereocontrol were made, however, changing the temperature of lithiation, the use of more bulky bases such as lithium tetramethylpiperidide, or the use of toluene as solvent produced little or no changes of diastereoselectivity.
  • 22
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    • note
    • (j) This is in agreement with the few existing reports on additions of metallated alkyl sulfoxides across the C-N double bonds of imines (see above, Refs. 5a-h), but in sharp contrast with the peculiar behaviour of α-lithium benzyl p-tolyl sulfoxide, which was found to react with the imine 2 almost exclusively via the syn-geometry (Ref. 3).
  • 24
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    • note
    • s)-stereochemistry. (figure presented)
  • 25
    • 85038554481 scopus 로고    scopus 로고
    • note
    • 2-3=3.6 Hz strongly suggests a trans pseudo-equatorial configuration, in full agreement with the expected configuration.
  • 29
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    • note
    • 4/pyridine is an efficient strategy for obtaining the corresponding desulfenylated derivatives, like 16, with syn-stereoselectivity: see Ref. 8c.
  • 32
    • 0000284525 scopus 로고
    • Müller, E., Ed.; Thieme Verlag: Stuttgart
    • The stereo selectivity of this reaction is quite surprising, since all the reactions of (R)-11 with alkyl, vinyl and phenyl Grignard reagents showed opposite stereocontrol, producing the corresponding anti-products, possibly originated from a highly effective 'chelation control' (Ref. 8b,c). An opposite stereochemical outcome (chelation control) was also reported for a wide range of reactions between N-monoprotected α-amino aldehydes and Grignard reagents, including allylic ones. See for example: (a) Devant, R. M.; Radunz, H.-E. In Houben-Weyl: Methods in Organic Synthesis; Müller, E., Ed.; Thieme Verlag: Stuttgart, 1995; Vol. E21b, pp. 1236-1239.
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  • 34
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    • Heathcock, C. H., Ed.; Pergamon Press: Oxford
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    • For recent examples see
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    • note
    • 13C NMR, mass spectrometry and microanalyses.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.