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Volumn 11, Issue 2, 2009, Pages 425-428

Formation and utility of azasilacyclopentadienes derived from silacyclopropenes and nitriles

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AMINOALCOHOL; BORIC ACID; CARBON; COPPER; CYCLOPENTANE DERIVATIVE; HETEROCYCLIC COMPOUND; NITRILE; SILICON;

EID: 61449131532     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802412b     Document Type: Article
Times cited : (19)

References (31)
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    • For reviews that include methods for the synthesis of allylic amines, see: a
    • For reviews that include methods for the synthesis of allylic amines, see: (a) Johannsen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1698-1708.
    • (1998) Chem. Rev , vol.98 , pp. 1698-1708
    • Johannsen, M.1    Jørgensen, K.A.2
  • 3
    • 62149147619 scopus 로고    scopus 로고
    • Carpenter, N. E. In Organic Reactions; Overman, L. E., Ed.; Wiley: New York, 2005; 66, pp 1-107. For examples of different methods for allylic amine synthesis, see:
    • (c) Carpenter, N. E. In Organic Reactions; Overman, L. E., Ed.; Wiley: New York, 2005; Vol. 66, pp 1-107. For examples of different methods for allylic amine synthesis, see:
  • 13
    • 34848818304 scopus 로고    scopus 로고
    • For the synthesis of an allylic amine via a silaaziridine intermediate, see
    • For the synthesis of an allylic amine via a silaaziridine intermediate, see: Nevárez, Z.; Woerpel, K. A. Org. Lett. 2007, 9, 3773-3776.
    • (2007) Org. Lett , vol.9 , pp. 3773-3776
    • Nevárez, Z.1    Woerpel, K.A.2
  • 16
    • 62149107941 scopus 로고    scopus 로고
    • All of the insertion products shown in Tables 1 and 2 were isolated and purified by a hexane extraction from an acetonitrile solution of the reaction mixture in an inert atmosphere glovebox. This procedure allowed the products to be separated from the copper catalyst and avoided hydrolysis of the Si-N bonds of these sensitive products. Additional confirmation of structure was obtained for the corresponding hydrolysis products; details are provided as Supporting Information.
    • All of the insertion products shown in Tables 1 and 2 were isolated and purified by a hexane extraction from an acetonitrile solution of the reaction mixture in an inert atmosphere glovebox. This procedure allowed the products to be separated from the copper catalyst and avoided hydrolysis of the Si-N bonds of these sensitive products. Additional confirmation of structure was obtained for the corresponding hydrolysis products; details are provided as Supporting Information.
  • 17
    • 62149115721 scopus 로고    scopus 로고
    • 1H NOESY experiments.
    • 1H NOESY experiments.
  • 18
    • 62149127079 scopus 로고    scopus 로고
    • For transition-metal-mediated reductive coupling reactions of alkynes and imines, see: (a) Reference 1d.
    • For transition-metal-mediated reductive coupling reactions of alkynes and imines, see: (a) Reference 1d.
  • 20
    • 62149128245 scopus 로고    scopus 로고
    • Reference 1g
    • Reference 1g.
  • 21
    • 62149116083 scopus 로고    scopus 로고
    • Details are provided as Supporting Information
    • Details are provided as Supporting Information.
  • 22
    • 36048951463 scopus 로고    scopus 로고
    • For recent examples of reductive amination under acidic conditions, see: a
    • For recent examples of reductive amination under acidic conditions, see: (a) Reddy, P. S.; Kanjilal, S.; Sunitha, S.; Prasad, R. B. N. Tetrahedron Lett. 2007, 48, 8807-8810.
    • (2007) Tetrahedron Lett , vol.48 , pp. 8807-8810
    • Reddy, P.S.1    Kanjilal, S.2    Sunitha, S.3    Prasad, R.B.N.4
  • 24
    • 62149150343 scopus 로고    scopus 로고
    • 3N or using silanized silica gel or alumina did not improve the purification.
    • 3N or using silanized silica gel or alumina did not improve the purification.
  • 25
    • 37049109987 scopus 로고    scopus 로고
    • For examples of additions of enamines to acrylonitrile and methyl acrylate, see: (a) de Jeso, B, Pommier, J.-C. J. Chem. Soc, Chem. Commun. 1977, 565-566
    • For examples of additions of enamines to acrylonitrile and methyl acrylate, see: (a) de Jeso, B.; Pommier, J.-C. J. Chem. Soc., Chem. Commun. 1977, 565-566.
  • 29
    • 6444221257 scopus 로고    scopus 로고
    • For examples of enamine hydroboration, see: (a) Butler, D. N, Soloway, A. H. J. Am. Chem. Soc. 1966, 88, 484-487
    • For examples of enamine hydroboration, see: (a) Butler, D. N.; Soloway, A. H. J. Am. Chem. Soc. 1966, 88, 484-487.
  • 31
    • 62149140249 scopus 로고    scopus 로고
    • The allylic amino alcohol was isolated in 85% yield with >90% purity. This compound was of sufficient purity to be used in subsequent reactions. Purification by chromatography provided a 44% yield of the allylic amino alcohol.
    • The allylic amino alcohol was isolated in 85% yield with >90% purity. This compound was of sufficient purity to be used in subsequent reactions. Purification by chromatography provided a 44% yield of the allylic amino alcohol.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.