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Volumn , Issue 22, 2009, Pages 3683-3687

1,1′-Binaphthyldiamine-based lewis bases as readily available and efficient grganocatalysts for the reduction of N-Aryl and N-Alkyl ketimines

Author keywords

Binaphthyldiamines; Enantioselectivity; Lewis bases; Organocatalysis; Reduction

Indexed keywords


EID: 67650683713     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900524     Document Type: Article
Times cited : (30)

References (36)
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    • For reviews on supported organic catalysts see: c
    • For reviews on supported organic catalysts see: c) A. Puglisi, F. Cozzi, M. Benaglia, Chem. Rev. 2003, 103, 3401-3430;
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    • Selected references: a A. V. Malkov, A. Mariani, K. N. Mac-Dougal, P. Kočovský, Org. Lett. 2004, 6, 2253;
    • Selected references: a) A. V. Malkov, A. Mariani, K. N. Mac-Dougal, P. Kočovský, Org. Lett. 2004, 6, 2253;
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    • P. Wu, Z. Wang, M. Cheng, L. Zhou, 1 Sun, Tetrahedron 2008, 64, 11304;
    • h) P. Wu, Z. Wang, M. Cheng, L. Zhou, 1 Sun, Tetrahedron 2008, 64, 11304;
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    • 59849094066 scopus 로고    scopus 로고
    • For a preliminary report on chiral diamine-derived Lewis bases in ketimine reductions see
    • For a preliminary report on chiral diamine-derived Lewis bases in ketimine reductions see: S. Guizzetti, M. Benaglia, F. Cozzi, S. Rossi, G. Celentano, Chirality 2009, 21, 233.
    • (2009) Chirality , vol.21 , pp. 233
    • Guizzetti, S.1    Benaglia, M.2    Cozzi, F.3    Rossi, S.4    Celentano, G.5
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    • The compound was easily prepared in a two steps, one purification only procedure in 90 % yield, see: M. C. Minimi, M. Gullotti, L. Santagostini, R. Pagliarin, L. De Gioia, E. Monzani, L. Casella, Eur. J. Inorg. Chem. 2003, 3934.
    • The compound was easily prepared in a two steps, one purification only procedure in 90 % yield, see: M. C. Minimi, M. Gullotti, L. Santagostini, R. Pagliarin, L. De Gioia, E. Monzani, L. Casella, Eur. J. Inorg. Chem. 2003, 3934.
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    • European Patent Application No. EP07023240.0, September 22, 2008
    • S. Guizzetti, M. Benaglia, European Patent Application No. EP07023240.0, September 22, 2008.
    • Guizzetti, S.1    Benaglia, M.2
  • 34
    • 67650699944 scopus 로고    scopus 로고
    • The use of the bisbenzamide of the 1,1′-binaphthyl diarnine as organocatalyst led to the formation of the chiral amine in only 20% yield and with no stereoselectivity, as clear demonstration of the fundamental role of the picolinamide moiety to guarantee high chemical and stereochemical efficiency of the catalyst
    • The use of the bisbenzamide of the 1,1′-binaphthyl diarnine as organocatalyst led to the formation of the chiral amine in only 20% yield and with no stereoselectivity, as clear demonstration of the fundamental role of the picolinamide moiety to guarantee high chemical and stereochemical efficiency of the catalyst.
  • 35
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    • The introduction of a substituent in the 3 or 6 position of the pyridine ring decreased the stereochemical efficiency of the catalyst, while substitution in the 4 position seems not to have any remarkable effect
    • The introduction of a substituent in the 3 or 6 position of the pyridine ring decreased the stereochemical efficiency of the catalyst, while substitution in the 4 position seems not to have any remarkable effect.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.