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Volumn 46, Issue 12, 2007, Pages 2078-2081

Pd-catalyzed cleavage of benzylic nitro bonds: New opportunities for asymmetric synthesis

Author keywords

Cleavage reactions; Nitro compounds; Palladium; Reduction; Synthetic methods

Indexed keywords

CHEMICAL BONDS; NITROGEN COMPOUNDS; PARAFFINS; SYNTHESIS (CHEMICAL);

EID: 34250865131     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200604263     Document Type: Article
Times cited : (32)

References (89)
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    • J. Tormo, D. H. Hays, G. C. Fu, J. Org. Chem. 1998, 63, 5296. We have subjected 1 to these catalytic conditions, although less than 50, conversion into 2 was observed after 24 h
    • J. Tormo, D. H. Hays, G. C. Fu, J. Org. Chem. 1998, 63, 5296. We have subjected 1 to these catalytic conditions, although less than 50 % conversion into 2 was observed after 24 h.
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    • 34250836047 scopus 로고    scopus 로고
    • for the single example of a reaction on a tertiary benzylic substrate, see: F.J. Stiefel, U.S. 486837, 1989.
    • b) for the single example of a reaction on a tertiary benzylic substrate, see: F.J. Stiefel, U.S. 486837, 1989.
  • 29
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    • The fact that deuterium incorporation does not occur at the benzylic site renders the process quite different to that observed with tertiary allylic organonitro compounds, in which the organonitro substrate leads to an organopalladium intermediate which can be intercepted by a range of nucleophiles including hydrides; see reference [6a
    • The fact that deuterium incorporation does not occur at the benzylic site renders the process quite different to that observed with tertiary allylic organonitro compounds, in which the organonitro substrate leads to an organopalladium intermediate which can be intercepted by a range of nucleophiles including hydrides; see reference [6a].
  • 31
    • 32244444791 scopus 로고    scopus 로고
    • For examples of asymmetric reactions which involve nitro-alkanes, see: a M. Terada, H. Ube, Y. Yaguchi, J. Am. Chem. Soc. 2006, 128, 1454, and references [8] and [9] therein;
    • For examples of asymmetric reactions which involve nitro-alkanes, see: a) M. Terada, H. Ube, Y. Yaguchi, J. Am. Chem. Soc. 2006, 128, 1454, and references [8] and [9] therein;
  • 34
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    • 33745211429 scopus 로고    scopus 로고
    • For examples of asymmetric reactions which involve nitro-olefins, see: a D. Enders, M. R. M. Hüttl, C. Grondal, G. Raabe, Nature 2006, 441, 861;
    • For examples of asymmetric reactions which involve nitro-olefins, see: a) D. Enders, M. R. M. Hüttl, C. Grondal, G. Raabe, Nature 2006, 441, 861;
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    • Angew. Chem. Int. Ed. 2006, 45, 5984;
    • (2006) Chem. Int. Ed , vol.45 , pp. 5984
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    • Angew. Chem. Int. Ed. 2005, 44, 6576;
    • (2005) Chem. Int. Ed , vol.44 , pp. 6576
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    • Compounds of the class represented by 1 can also be accessed enantioselectively by conjugate addition of a phenyl lithium species to (E)-(1-nitrobut-1-enyl)benzene in the presence of sparteine; see: a) M. Yamahita, K. Yamada, K. Tomioka, J. Am. Chem. Soc. 2004, 126, 1954;
    • Compounds of the class represented by 1 can also be accessed enantioselectively by conjugate addition of a phenyl lithium species to (E)-(1-nitrobut-1-enyl)benzene in the presence of sparteine; see: a) M. Yamahita, K. Yamada, K. Tomioka, J. Am. Chem. Soc. 2004, 126, 1954;
  • 83
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    • In a related approach which involves β-amido nitroalkanes, the nitro group was reduced using stoichiometric amounts of Bu3SnH and AIBN; see: M.-L. Leroux, T. LeGall, C. Mioskowski, Tetrahedron: Asymmetry 2001, 12, 1817;
    • 3SnH and AIBN; see: M.-L. Leroux, T. LeGall, C. Mioskowski, Tetrahedron: Asymmetry 2001, 12, 1817;
  • 87


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.