메뉴 건너뛰기




Volumn , Issue 8, 2001, Pages 1449-1458

Synthesis of nonracemic α-trifluoromethyl α-amino acids from sulfinimines of trifluoropyruvate

Author keywords

Amino acids; Asymmetric synthesis; Grignard reactions; Sulfinimines; Trifluoromethyl group

Indexed keywords

AMINO ACID DERIVATIVE; FLUORINE DERIVATIVE; IMINE; PYRUVIC ACID DERIVATIVE;

EID: 0035048927     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200104)2001:8<1449::aid-ejoc1449>3.0.co;2-2     Document Type: Article
Times cited : (69)

References (86)
  • 15
  • 17
  • 19
    • 0005181649 scopus 로고    scopus 로고
    • Chem. Abstr. 109: 55185p.
    • Chem. Abstr. , vol.109 , pp. 55185
  • 26
    • 85088882952 scopus 로고    scopus 로고
    • [9], p. 267-294
    • [9], p. 267-294.
  • 31
    • 0002515790 scopus 로고    scopus 로고
    • Synthesis of Nonracemic β-Amino Acids via Chiral Sulfinimines
    • (Ed.: E. Juaristi), Wiley-VCH: Chichester
    • [15a] F. A. Davis, R. E. Reddy, "Synthesis of Nonracemic β-Amino Acids via Chiral Sulfinimines" in: Enantioselective Synthesis of β-Amino Acids (Ed.: E. Juaristi), Wiley-VCH: Chichester, 1997, p. 127-138.
    • (1997) Enantioselective Synthesis of β-Amino Acids , pp. 127-138
    • Davis, F.A.1    Reddy, R.E.2
  • 44
    • 84914209165 scopus 로고
    • Racemic sulfinimines derived from trifluoromethyl ketones have been described, but those synthetic methodologies are likely to be incompatible with the preparation of nonracemic products, due to the harsh conditions employed: [17a] R. Mews, P. Kricke, I. Stahl, Z. Naturforsch., Teil B 1981, 36, 1093-1098 and references therein.
    • (1981) Z. Naturforsch., Teil B , vol.36 , pp. 1093-1098
    • Mews, R.1    Kricke, P.2    Stahl, I.3
  • 60
    • 33847799061 scopus 로고
    • For a discussion of the configurational and stereochemical properties of ketone-derived sulfinimines, see: [24a] F. A. Davis, E. W. Kluger, J. Am. Chem. Soc. 1976, 98, 302-303 and references therein.
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 302-303
    • Davis, F.A.1    Kluger, E.W.2
  • 63
    • 85088883113 scopus 로고    scopus 로고
    • [21c]
    • [21c]
  • 66
    • 0005175413 scopus 로고    scopus 로고
    • unpublished results
    • [25c] S. V. Meille, unpublished results.
    • Meille, S.V.1
  • 69
    • 0005220657 scopus 로고    scopus 로고
    • note
    • It is worth noting that isopropylmagnesium chloride did not promote reduction of the C=N bond of (S)-1b, in sharp contrast with the reactions between isopropylmagnesium halides and N-alkoxycarbonyl imines of trifluoropyruvate, in which 40% of reduction occurs (see ref. [5a]).
  • 70
    • 0005127169 scopus 로고    scopus 로고
    • note
    • The ee values were determined by chiral HPLC analysis of both enantiomers of sulfinamides 12 and 13, performed with a Chiralcel OD column, using n-hexane/isppropyl alcohol, 85:15, as eluent, with a flow rate of 0.8 mL/min.
  • 71
    • 0005162367 scopus 로고    scopus 로고
    • note
    • 2 through the solvent, or adding traces of water, did not produce any conclusion. However, this undesired event turned out to be useful, because crystallization of sulfinamides 12 and 13 of low ee occurs much more effectively, providing diastereomerically pure racemic crystals suitable for X-ray diffraction, while sulfinamides of high ee were much less prone to crystallization.
  • 82
    • 85088883070 scopus 로고    scopus 로고
    • note
    • 2 hybridization and intermolecular hydrogen bonds involve the amidic hydrogen with the sulfoxide oxygen. The two independent molecules in the crystal of 12d exhibit only marginal but significant differences (5-10°) in torsion angles, suggesting that the structure determined is close to the minimum energy conformation.
  • 84
    • 85088882553 scopus 로고    scopus 로고
    • [12]
    • [12]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.