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Volumn 11, Issue 23, 2009, Pages 5390-5393

Desymmetrization of cyclic meso-epoxides with silicon tetrachloride catalyzed by PINDOX, a chiral bipyridine mono-N-oxide

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EID: 72449165875     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902148s     Document Type: Article
Times cited : (41)

References (39)
  • 2
    • 72449121696 scopus 로고
    • Chem. Abstr. 1958, 52, 44711.
    • (1958) Chem. Abstr. , vol.52 , pp. 44711
  • 10
    • 72449186422 scopus 로고    scopus 로고
    • See also footnote 13 in ref 11.
    • (b) See also footnote 13 in ref 11.
  • 12
    • 84891036468 scopus 로고    scopus 로고
    • Chiral Lewis bases as catalysts
    • Dalko, P. I., Ed.; Wiley-VCH: Weinheim
    • For overviews, see: (a) Kočovský, P.; Malkov, A. V. Chiral Lewis Bases as Catalysts. In Enantioselective Organocatalysis; Dalko, P. I., Ed.; Wiley-VCH: Weinheim, 2007; p 255.
    • (2007) Enantioselective Organocatalysis , pp. 255
    • Kočovský, P.1    Malkov, A.V.2
  • 18
    • 68049088920 scopus 로고    scopus 로고
    • For the most recent application of axially chiral allene-derived phosphine oxides, see: (c) Pu, X.; Qi, X.; Ready. J. M. J. Am. Chem. Soc. 2009, 131, 10364.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 10364
    • Pu, X.1    Qi, X.2    Ready, J.M.3
  • 25
    • 72449161437 scopus 로고    scopus 로고
    • The absolute configuration of chlorohydrins 10 is unknown; the formulae shown here merely represent an arbitrarily chosen enantiomer.
    • (a) The absolute configuration of chlorohydrins 10 is unknown; the formulae shown here merely represent an arbitrarily chosen enantiomer.
  • 26
    • 72449195567 scopus 로고    scopus 로고
    • 19F NMR analysis of the corresponding Mosher's esters, as most of the chlorohydrins 10 (except 10c) proved difficult to separate by chiral chromatography.
    • 19F NMR analysis of the corresponding Mosher's esters, as most of the chlorohydrins 10 (except 10c) proved difficult to separate by chiral chromatography.
  • 27
    • 72449149017 scopus 로고    scopus 로고
    • 1H NMR spectra of the crude products, which excludes a possible ee amplification during this derivatization.
    • 1H NMR spectra of the crude products, which excludes a possible ee amplification during this derivatization.
  • 28
    • 72449134643 scopus 로고    scopus 로고
    • The enantiopurity of Mosher's acid was independently verified to be >99% ee (see the Supporting Information).
    • The enantiopurity of Mosher's acid was independently verified to be >99% ee (see the Supporting Information).
  • 29
    • 72449137939 scopus 로고    scopus 로고
    • Chiral GC analysis of the trifluoroacetate derived from 10c revealed 87% ee, which is in good agreement with the the value obtained by the Mosher method (90% ee).
    • Chiral GC analysis of the trifluoroacetate derived from 10c revealed 87% ee, which is in good agreement with the the value obtained by the Mosher method (90% ee).
  • 32
    • 72449165725 scopus 로고    scopus 로고
    • note
    • 8).
  • 38
    • 0000542506 scopus 로고
    • but differ from those recorded for the vicinal chlorohydrin (also described by Waegell)
    • 13c However, he formulated the product as a vicinal chlorohydrin, which is apparently incorrect, as revealed by his NMR spectra that are compatible with those for 11 (as reported here and by Waegell: Chauvet, F.: Heumann, A.; Waegell, B. J. Org. Chem. 1987, 52, 1916.) but differ from those recorded for the vicinal chlorohydrin (also described by Waegell)
    • (1987) J. Org. Chem. , vol.52 , pp. 1916
    • Chauvet, F.1    Heumann, A.2    Waegell, B.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.