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Volumn 9, Issue 19, 2007, Pages 3773-3776

Metal-catalyzed silylene transfer to imines: Synthesis and reactivity of silaaziridines

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; ALLYL COMPOUND; AZIRIDINE DERIVATIVE; IMINE; PALLADIUM; SILANE DERIVATIVE; SILVER;

EID: 34848818304     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701424a     Document Type: Article
Times cited : (32)

References (42)
  • 8
    • 84868264013 scopus 로고    scopus 로고
    • 4, and AgOTf gave products in comparable yields. Copper catalysts at higher temperatures also provided products, although in low yields.
    • 4, and AgOTf gave products in comparable yields. Copper catalysts at higher temperatures also provided products, although in low yields.
  • 9
    • 0037077611 scopus 로고    scopus 로고
    • For examples of mejal-catalyzed silylene transfer to mono- and disubstituted alkenes, see: Ćiraković, J, Driver, T. G, Woerpel, K. A. J. Am. Chem. Soc. 2002, 124, 9370-9371
    • For examples of mejal-catalyzed silylene transfer to mono- and disubstituted alkenes, see: Ćiraković, J.: Driver, T. G.; Woerpel, K. A. J. Am. Chem. Soc. 2002, 124, 9370-9371.
  • 10
    • 0001931827 scopus 로고    scopus 로고
    • Formal [4+1 ] products have been observed for other silylene transfer reactions to unsaturated imines and dienes: (a) Bobbitt, K. L.; Gaspar, P. P. J. Organomet. Chem. 1995, 499, 17-26.
    • Formal [4+1 ] products have been observed for other silylene transfer reactions to unsaturated imines and dienes: (a) Bobbitt, K. L.; Gaspar, P. P. J. Organomet. Chem. 1995, 499, 17-26.
  • 11
    • 0000873992 scopus 로고    scopus 로고
    • Vinylsilacyclopropanes, however, have been prepared: Zhang, S.; Conlin, R. T. J. Am. Chem. Soc. 1991, 113, 4272-4278.
    • (b) Vinylsilacyclopropanes, however, have been prepared: Zhang, S.; Conlin, R. T. J. Am. Chem. Soc. 1991, 113, 4272-4278.
  • 12
    • 34848838268 scopus 로고    scopus 로고
    • The details are provided as Supporting Information
    • The details are provided as Supporting Information.
  • 13
    • 13944263884 scopus 로고    scopus 로고
    • The analogous reaction was observed for α,β-unsaturated esters and ketones: Calad, S. A.; Woerpel, K. A. J. Am. Chem. Soc. 2005, 127, 2046-2047 and references therein.
    • The analogous reaction was observed for α,β-unsaturated esters and ketones: Calad, S. A.; Woerpel, K. A. J. Am. Chem. Soc. 2005, 127, 2046-2047 and references therein.
  • 15
    • 34848849324 scopus 로고    scopus 로고
    • Product 14 was also obtained in the absence of a silver catalyst, although the reaction was slower and low-yielding
    • Product 14 was also obtained in the absence of a silver catalyst, although the reaction was slower and low-yielding.
  • 16
    • 34848837006 scopus 로고    scopus 로고
    • Upon purification of 14 by flash chromatography, a significant amount of N.O-acetal hydrolysis and elimination to form 14′ were observed. Vinyl silane 14′ was isolated in 13% yield.
    • Upon purification of 14 by flash chromatography, a significant amount of N.O-acetal hydrolysis and elimination to form 14′ were observed. Vinyl silane 14′ was isolated in 13% yield.
  • 17
    • 34848889564 scopus 로고    scopus 로고
    • Purification of 15 by flash chromatography gave a mixture of hydrolyzed products. Compound 15' was isolated in 55% yield. Figure presented
    • Purification of 15 by flash chromatography gave a mixture of hydrolyzed products. Compound 15' was isolated in 55% yield. Figure presented
  • 19
    • 0347088930 scopus 로고    scopus 로고
    • For other transition-metal-mediated alkyne insertion reactions of strained intermediates, see: a
    • For other transition-metal-mediated alkyne insertion reactions of strained intermediates, see: (a) Barluenga, J.; Rodríguez, F.; Álvarez-Rodrigo, L.; Zapico, J. M.; Fañanás, F. J. Chem. Eur. J. 2004, 10, 109-116.
    • (2004) Chem. Eur. J , vol.10 , pp. 109-116
    • Barluenga, J.1    Rodríguez, F.2    Álvarez-Rodrigo, L.3    Zapico, J.M.4    Fañanás, F.J.5
  • 38
    • 33744757356 scopus 로고    scopus 로고
    • For other metal-catalyzed reductive coupling strategies of imines and alkynes, see: a
    • For other metal-catalyzed reductive coupling strategies of imines and alkynes, see: (a) Black, D. A.; Arndtsen, B. A. Org. Lett. 2006, 8, 1991-1993.
    • (2006) Org. Lett , vol.8 , pp. 1991-1993
    • Black, D.A.1    Arndtsen, B.A.2
  • 40
    • 34848871565 scopus 로고    scopus 로고
    • See ref. 20c
    • (c) See ref. 20c.
  • 41
    • 84868263596 scopus 로고    scopus 로고
    • -1) for the Si-H are similar to other aminosilanes: Gu, T.-Y. Y.; Weber, W. P. J. Organomet. Chem. 1980, 184, 7-11.
    • -1) for the Si-H are similar to other aminosilanes: Gu, T.-Y. Y.; Weber, W. P. J. Organomet. Chem. 1980, 184, 7-11.
  • 42
    • 84868265425 scopus 로고    scopus 로고
    • A 1,3-dipolar cycloaddition between dipole III (Scheme 3) and an alkyne would also account for the formation of compounds 16a-f. We have not, however, observed the cycloaddition under thermal conditions 120°C
    • A 1,3-dipolar cycloaddition between dipole III (Scheme 3) and an alkyne would also account for the formation of compounds 16a-f. We have not, however, observed the cycloaddition under thermal conditions (120°C).


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