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Volumn 132, Issue 9, 2010, Pages 2860-2861

N-Heterocyclic carbene catalyzed asymmetrichydration: Direct svnthesis of α-protio and α-deuterio α-chloro and α-fluoro carboxylic acids

Author keywords

[No Author keywords available]

Indexed keywords

N-HETEROCYCLIC CARBENES; REDOX PROCESS;

EID: 77950372661     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja910281s     Document Type: Article
Times cited : (150)

References (40)
  • 14
    • 78649374767 scopus 로고    scopus 로고
    • DOI:10.1007/128-2008-18
    • For reviews on NHC catalysis, see: (a) Moore, J. L.; Rovis, T. Top. Curr. Chem. 2009, 297, DOI:10.1007/128-2008-18.
    • (2009) Top. Curr. Chem. , vol.297
    • Moore, J.L.1    Rovis, T.2
  • 21
    • 33748807069 scopus 로고    scopus 로고
    • For an example of an α-redox reaction conducted under biphasic conditions, see
    • For a single example of water participating as a nucleophile with the acyl azolium, see: (a) Sohn, S. S.; Bode, J. W. Angew. Chem., Int. Ed. 2006, 45, 6021-6024. For an example of an α-redox reaction conducted under biphasic conditions, see:
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 6021-6024
    • Sohn, S.S.1    Bode, J.W.2
  • 22
    • 55949132381 scopus 로고    scopus 로고
    • For reactivity of NHC with water see
    • (b) He, M.; Beahm, B. J.; Bode, J. W. Org. Lett. 2008, 10, 3817-3820. For reactivity of NHC with water see:
    • (2008) Org. Lett. , vol.10 , pp. 3817-3820
    • He, M.1    Beahm, B.J.2    Bode, J.W.3
  • 25
    • 77950413019 scopus 로고    scopus 로고
    • With 5 mol % catalyst, we observe no conversion after 12 h
    • With 5 mol % catalyst, we observe no conversion after 12 h.
  • 29
    • 77950388578 scopus 로고    scopus 로고
    • Absolute stereochemistry has been assigned by chemical correlation to adducts obtained from phenol addition to the haloaldehydes; see the Supporting Information
    • Absolute stereochemistry has been assigned by chemical correlation to adducts obtained from phenol addition to the haloaldehydes; see the Supporting Information.
  • 30
    • 77950429945 scopus 로고    scopus 로고
    • A large-scale (1.5 g of cyclopentylmethyldichloroacetaldehyde) reaction affords 2d in 84% yield and 95% ee
    • A large-scale (1.5 g of cyclopentylmethyldichloroacetaldehyde) reaction affords 2d in 84% yield and 95% ee.
  • 36
    • 77950441146 scopus 로고    scopus 로고
    • (Z)-α-Fluoro-p-methoxyphenylacrylaldehyde provides 4a in 93% ee and 84% yield, while the E substrate provides 4a in 93% ee and 42% yield under identical conditions
    • (Z)-α-Fluoro-p-methoxyphenylacrylaldehyde provides 4a in 93% ee and 84% yield, while the E substrate provides 4a in 93% ee and 42% yield under identical conditions.
  • 37
    • 77950451195 scopus 로고    scopus 로고
    • Aldehyde purity plays an integral role in the enantioselectivities observed
    • Aldehyde purity plays an integral role in the enantioselectivities observed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.