메뉴 건너뛰기




Volumn 2014, Issue 25, 2014, Pages 5397-5417

Complexation Phenomena and Dynamics at Work in the Lithiation Reactions of Small-Ring Heterocycles: Regio- and Stereoselectivity

Author keywords

Carbenoids; Lithiation; Nitrogen heterocycles; Oxygen heterocycles; Reaction mechanisms

Indexed keywords


EID: 84934889646     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201402744     Document Type: Article
Times cited : (16)

References (139)
  • 1
    • 84953353898 scopus 로고    scopus 로고
    • The Chemistry of Organolithium Compounds (Eds.:, Wiley-VCH, Weinheim, Germany.
    • The Chemistry of Organolithium Compounds (Eds.:, Z. Rappoport, I. Marek), Wiley-VCH, Weinheim, Germany, 2004.
    • (2004)
    • Rappoport, Z.1    Marek, I.2
  • 6
    • 84927055870 scopus 로고    scopus 로고
    • Lithium Compounds in Organic Synthesis - From Fundamentals to Applications (Eds.:, Wiley-VCH, Weinheim, Germany.
    • Lithium Compounds in Organic Synthesis-From Fundamentals to Applications (Eds.:, R. Luisi, V. Capriati), Wiley-VCH, Weinheim, Germany, 2014.
    • (2014)
    • Luisi, R.1    Capriati, V.2
  • 10
    • 4544276592 scopus 로고    scopus 로고
    • Angew. Chem. 1998, 110, 444
    • (1998) Angew. Chem. , vol.110 , pp. 444
  • 12
    • 84953347053 scopus 로고    scopus 로고
    • in: (Eds.:, Contemporary Carbene Chemistry, Wiley, New York, chapter 11, p. 327-362.
    • V. Capriati, in: Modern Lithium Carbenoid Chemistry (Eds.:, R. A. Moss, M. P. Doyle), Contemporary Carbene Chemistry, Wiley, New York, 2014, chapter 11, p. 327-362.
    • (2014) Modern Lithium Carbenoid Chemistry
    • Capriati, V.1    Moss, R.A.2    Doyle, M.P.3
  • 13
    • 0004057748 scopus 로고    scopus 로고
    • Fischer-type carbenes, for example, are typical electrophilic complexes, whereas Schrock-type carbenes exhibit nucleophilic reactivity; for a survey, see:, in: Wiley-VCH, Weinheim, Germany.
    • Fischer-type carbenes, for example, are typical electrophilic complexes, whereas Schrock-type carbenes exhibit nucleophilic reactivity; for a survey, see:, F. Z. Dörwald, in: Metal Carbenes in Organic Synthesis Wiley-VCH, Weinheim, Germany, 1999.
    • (1999) Metal Carbenes in Organic Synthesis
    • Dörwald, F.Z.1
  • 15
    • 84953363814 scopus 로고    scopus 로고
    • Topics in Stereochemistry: Stereochemical Aspects of Organolithium Compounds (Ed.:, Wiley-VCH, Weinheim, Germany.
    • Topics in Stereochemistry: Stereochemical Aspects of Organolithium Compounds (Ed.:, R. E. Gawley), Wiley-VCH, Weinheim, Germany, 2010.
    • (2010)
    • Gawley, R.E.1
  • 16
    • 84953364622 scopus 로고    scopus 로고
    • For leading reviews on ortho-lithiation
    • For leading reviews on ortho-lithiation, see:
  • 20
    • 15044354362 scopus 로고    scopus 로고
    • Angew. Chem. 2004, 116, 2256
    • (2004) Angew. Chem. , vol.116 , pp. 2256
  • 24
    • 0001318042 scopus 로고    scopus 로고
    • T. Satoh, Chem. Rev. 1996, 96, 3303-3325.
    • (1996) Chem. Rev. , vol.96 , pp. 3303-3325
    • Satoh, T.1
  • 27
    • 0242475011 scopus 로고    scopus 로고
    • For a special issue on oxiranyl and aziridinyl anions
    • , see: , Tetrahedron Symposia-in-Print (Ed.: S. Florio), Tetrahedron
    • for a special issue on oxiranyl and aziridinyl anions, see: Oxiranyl and Aziridinyl Anions as Reactive Intermediates in Synthetic Organic Chemistry, Tetrahedron Symposia-in-Print (Ed.: S. Florio), Tetrahedron 2003, 59, 9693-9684.
    • (2003) Oxiranyl and Aziridinyl Anions As Reactive Intermediates in Synthetic Organic Chemistry , vol.59 , pp. 9693-9694
  • 28
    • 77955903246 scopus 로고    scopus 로고
    • A. Salomone in: Topics in Stereochemistry, 26: Stereochemical Aspects of Organolithium Compounds (Eds.:, Wiley-VCH, Weinheim, Germany, p. 135-164.
    • V. Capriati, S. Florio, A. Salomone Oxiranyllithiums as Chiral Synthons for Asymmetric Synthesis in: Topics in Stereochemistry, vol. 26: Stereochemical Aspects of Organolithium Compounds (Eds.:, R. E. Gawley, J. S. Siegel), Wiley-VCH, Weinheim, Germany, 2010, p. 135-164.
    • (2010) Oxiranyllithiums As Chiral Synthons for Asymmetric Synthesis
    • Capriati, V.1    Florio, S.2    Gawley, R.E.3    Siegel, J.S.4
  • 67
    • 84917732445 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 7650
    • (2012) Angew. Chem. , vol.124 , pp. 7650
  • 74
    • 84953364716 scopus 로고    scopus 로고
    • Angew. Chem. 2010, 122, 9578
    • (2010) Angew. Chem. , vol.122 , pp. 9578
  • 76
    • 84858685773 scopus 로고    scopus 로고
    • for analogy results reported for nitrogen-containing heterocycles (pyrrolidines), see:, A. J. H. M. Meijer.
    • for analogy results reported for nitrogen-containing heterocycles (pyrrolidines), see:, N. S. Sheikh, D. Leonori, G. Barker, J. D. Firth, K. R. Campos, A. J. H. M. Meijer, P. O'Brien, I. Coldham, J. Am. Chem. Soc. 2012, 134, 5300-5308.
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 5300-5308
    • Sheikh, N.S.1    Leonori, D.2    Barker, G.3    Firth, J.D.4    Campos, K.R.5    O'Brien, P.6    Coldham, I.7
  • 83
    • 84886639511 scopus 로고    scopus 로고
    • Angew. Chem. 2013, 125, 3152
    • (2013) Angew. Chem. , vol.125 , pp. 3152
  • 98
    • 84957871647 scopus 로고    scopus 로고
    • Angew. Chem. 2009, 121, 1169
    • (2009) Angew. Chem. , vol.121 , pp. 1169
  • 100
    • 84953367468 scopus 로고    scopus 로고
    • Angew. Chem. 2007, 119, 2295
    • (2007) Angew. Chem. , vol.119 , pp. 2295
  • 116
    • 84928747980 scopus 로고    scopus 로고
    • Angew. Chem. 2010, 122, 2962
    • (2010) Angew. Chem. , vol.122 , pp. 2962
  • 128
    • 33845376843 scopus 로고
    • F. A. L. Anet.
    • F. A. L. Anet, J. Am. Chem. Soc. 1985, 107, 4335-4337.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 4335-4337
  • 130
    • 85013858414 scopus 로고    scopus 로고
    • The energy required for the N-inversion is expected to be in the range 9-12 kcal/mol much higher than that required for the ring puckering falling in the range 2-3 kcal/mol, see:, in:, 3rd ed., Elsevier, Oxford, UK, p. 210-237.
    • The energy required for the N-inversion is expected to be in the range 9-12 kcal/mol much higher than that required for the ring puckering falling in the range 2-3 kcal/mol, see:, A. R. Katritzky, C. A. Ramsden, J. Joule, V. V. Zhdankin, in: Handbook of Heterocyclic Chemistry, 3rd ed., Elsevier, Oxford, UK, 2010; p. 210-237.
    • (2010) Handbook of Heterocyclic Chemistry
    • Katritzky, A.R.1    Ramsden, C.A.2    Joule, J.3    Zhdankin, V.V.4
  • 139
    • 80054847382 scopus 로고    scopus 로고
    • Examples of preferential conformations in substituted aziridines have been recently reported.
    • Examples of preferential conformations in substituted aziridines have been recently reported:, M. C. de Ceglie, L. Degennaro, A. Falcicchio, R. Luisi, Tetrahedron 2011, 67, 9382-9388.
    • (2011) Tetrahedron , vol.67 , pp. 9382-9388
    • De Ceglie, M.C.1    Degennaro, L.2    Falcicchio, A.3    Luisi, R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.