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Volumn 76, Issue 1, 2011, Pages 285-288

Reversal of diastereoselectivity in reactions of the trifluoroacetaldehyde ethyl hemiacetal with enamines and imines: Metal-free, complementary anti-and syn-selective synthesis of 4,4,4-trifluoro-1-aryl-3-hydroxy-2-methyl-1-butanones

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREO-SELECTIVITY; ENAMINES; HEMIACETALS; SELECTIVE SYNTHESIS; TRIFLUOROACETALDEHYDE;

EID: 78650860332     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101733j     Document Type: Article
Times cited : (6)

References (24)
  • 1
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    • A recent book, see:;, Ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim.
    • A recent book, see: Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2004.
    • (2004) Modern Aldol Reactions
    • Mahrwald, R.1
  • 2
    • 35548984503 scopus 로고    scopus 로고
    • For recent examples of α-methyl-, chloro-, and fluoro- alkoxy-, hydroxy-aliphatic ketones, syn -adducts, see
    • For recent examples of α-methyl-, chloro-, and fluoro- alkoxy-, hydroxy-aliphatic ketones, syn -adducts, see: Xu, X.-Y.; Wang, Y.-Z.; Gong, L.-Z. Org. Lett. 2007, 9, 4247
    • (2007) Org. Lett. , vol.9 , pp. 4247
    • Xu, X.-Y.1    Wang, Y.-Z.2    Gong, L.-Z.3
  • 9
    • 77954135235 scopus 로고    scopus 로고
    • For recent examples of α-alkylated aldehydes, syn -adducts, see:;, For anti -adductts, see:; Angew. Chem., Int. Ed. 2004, 43, 2152
    • For recent examples of α-alkylated aldehydes, syn -adducts, see: Li, J.; Fu, N.; Li, X.; Luo, S.; Cheng, J.-P. J. Org. Chem. 2010, 75, 4501 For anti -adductts, see: Northrup, A. B.; Mangion, I. K.; Hettche, F.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2004, 43, 2152
    • (2010) J. Org. Chem. , vol.75 , pp. 4501
    • Li, J.1    Fu, N.2    Li, X.3    Luo, S.4    Cheng, J.-P.5    Northrup, A.B.6    Mangion, I.K.7    Hettche, F.8    MacMillan, D.W.C.9
  • 10
    • 2942641357 scopus 로고    scopus 로고
    • For organocatalytic asymmetric direct aldol reaction of aromatic methyl ketones, see
    • For organocatalytic asymmetric direct aldol reaction of aromatic methyl ketones, see: Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 1983
    • Torii, H.1    Nakadai, M.2    Ishihara, K.3    Saito, S.4    Yamamoto, H.5
  • 16
    • 78650856162 scopus 로고    scopus 로고
    • Ed.; ACS Symposium Series 911; Oxford University Press/American Chemical Society: Washington, DC,; p.
    • Funabiki, K. In Fluorine-Containing Synthons; Soloshonok, V., Ed.; ACS Symposium Series 911; Oxford University Press/American Chemical Society: Washington, DC, 2005; p 342.
    • (2005) Fluorine-Containing Synthons , pp. 342
    • Funabiki, K.1    Soloshonok, V.2
  • 19
    • 78650883792 scopus 로고    scopus 로고
    • ACS Symposium Series 949; Oxford University Press/American Chemical Society: Washington, DC,; p. Saito and Yamamoto also reported the same results of chloral with cycloalkanones; see ref 4a.
    • Funabiki, K.; Matsui, M. Current Fluoroorganic Chemistry; Soloshonok, V.; Mikami, K.; Yamazaki, T.; Welch, J. T.; Honek, J. F., Eds.; ACS Symposium Series 949; Oxford University Press/American Chemical Society: Washington, DC, 2007; p 141. Saito and Yamamoto also reported the same results of chloral with cycloalkanones; see ref 4a.
    • (2007) Current Fluoroorganic Chemistry , pp. 141
    • Funabiki, K.1    Matsui, M.2    Soloshonok, V.3    Mikami, K.4    Yamazaki, T.5    Welch, J.T.6    Honek, J.F.7
  • 20
    • 0001041017 scopus 로고    scopus 로고
    • The relative configurations were determined by NMR, according to the literature
    • The relative configurations were determined by NMR, according to the literature: Ishii, A.; Kojima, J.; Mikami, K. Org. Lett. 1999, 1, 2013
    • (1999) Org. Lett. , vol.1 , pp. 2013
    • Ishii, A.1    Kojima, J.2    Mikami, K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.