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Volumn 72, Issue 25, 2007, Pages 9704-9712

Dearomatizing anionic cyclization of N-alkyl-N-benzyl(dinaphthyl) phosphinamides. A facile route to γ-(amino)dihydronaphthalenylphosphinic acids

Author keywords

[No Author keywords available]

Indexed keywords

DEAROMATIZING ANIONIC CYCLIZATION; DIASTEREOSELECTIVITY; ELECTROPHILES; MICROMOLAR SCALE;

EID: 36849059697     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701607s     Document Type: Article
Times cited : (10)

References (70)
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    • DAr reactions based on complexation of aromatic π-systems to transition metals, see: (a) Brooks, B. C.; Gunnoe, T. B.; Harman, W. D. Coord. Chem. Rev. 2000, 206-207, 3.
    • DAr reactions based on complexation of aromatic π-systems to transition metals, see: (a) Brooks, B. C.; Gunnoe, T. B.; Harman, W. D. Coord. Chem. Rev. 2000, 206-207, 3.
  • 26
    • 33749537256 scopus 로고    scopus 로고
    • Harmata, M, Ed, Elsevier: Amsterdam, The Netherlands, Chapter 4, pp
    • (a) Clayden, J. In Strategies and Tactics in Organic Synthesis; Harmata, M., Ed.; Elsevier: Amsterdam, The Netherlands, 2004; Vol. 4, Chapter 4, pp 71-96.
    • (2004) Strategies and Tactics in Organic Synthesis , vol.4 , pp. 71-96
    • Clayden, J.1
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    • 0842325562 scopus 로고    scopus 로고
    • For 10a (bp 165°C/0.15 Torr), see: Imbery, D.; Friebolin, H. Z. Naturforsch. B 1968, 23, 759.
    • (a) For 10a (bp 165°C/0.15 Torr), see: Imbery, D.; Friebolin, H. Z. Naturforsch. B 1968, 23, 759.
  • 50
    • 36849049133 scopus 로고    scopus 로고
    • 3) = 138.1 ppm), see: Gouesnard, J. P.; Dorie, J.; Martin, G. J. Can. J. Chem. 1980, 58, 1295.
    • 3) = 138.1 ppm), see: Gouesnard, J. P.; Dorie, J.; Martin, G. J. Can. J. Chem. 1980, 58, 1295.
  • 51
    • 36849016763 scopus 로고    scopus 로고
    • 3 was added to a toluene solution of N-methylbenzylamine and triethylamine (2.5 equiv) at -78°C, and the mixture was stirred for 30 min at this temperature.
    • 3 was added to a toluene solution of N-methylbenzylamine and triethylamine (2.5 equiv) at -78°C, and the mixture was stirred for 30 min at this temperature.
  • 52
    • 0000063304 scopus 로고
    • For other examples of Grignard addition to aminodichlorophosphines, see: a, Jr
    • For other examples of Grignard addition to aminodichlorophosphines, see: (a) Burg.; A. B.; Slota, P. J., Jr. J. Am. Chem. Soc. 1958, 80, 1107.
    • (1958) J. Am. Chem. Soc , vol.80 , pp. 1107
    • Burg, A.B.1    Slota, P.J.2
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    • 2.
    • 2.
  • 55
    • 36849027529 scopus 로고    scopus 로고
    • 31P, DEPT, selective gTOCSY) and 2D (gCOSY45, gHMQC, gHMBC, and gNOESY) NMR experiments. See Supporting Information for structural characterization.
    • 31P, DEPT, selective gTOCSY) and 2D (gCOSY45, gHMQC, gHMBC, and gNOESY) NMR experiments. See Supporting Information for structural characterization.
  • 56
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    • 2 were also used as the proton source.
    • 2 were also used as the proton source.
  • 61
    • 36849054968 scopus 로고    scopus 로고
    • In the reaction of 17a with Me3O+BF 4, small amounts of rearomatized byproducts 22 and 23 are also formed Table 2, entry 6
    • -, small amounts of rearomatized byproducts 22 and 23 are also formed (Table 2, entry 6).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.