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Volumn 13, Issue 9, 2011, Pages 2248-2251

Three-component and nonclassical reaction of phosphines with enynes and aldehydes: Formation of γ-lactones featuring α-phosphorus ylides

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EID: 79955634183     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200527t     Document Type: Article
Times cited : (37)

References (57)
  • 9
    • 70349896036 scopus 로고    scopus 로고
    • Selected examples, see
    • Selected examples, see: Smith, S. W.; Fu, G. C. J. Am. Chem. Soc. 2009, 131, 14231
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 14231
    • Smith, S.W.1    Fu, G.C.2
  • 31
    • 33846805734 scopus 로고    scopus 로고
    • For a review, see:, For selected examples of α-Michael additions, see:;;;;; Org. Lett. 2010, 12, 244
    • For a review, see: Lewandowska, E. Tetrahedron 2007, 63, 2107 For selected examples of α-Michael additions, see: Li, Y.; Xu, X.; Tan, J.; Liao, P.; Zhang, J.; Liu, Q. Org. Lett. 2010, 12, 244
    • (2007) Tetrahedron , vol.63 , pp. 2107
    • Lewandowska, E.1    Li, Y.2    Xu, X.3    Tan, J.4    Liao, P.5    Zhang, J.6    Liu, Q.7
  • 39
    • 79955632324 scopus 로고    scopus 로고
    • Reactions with aldehydes, such as benzaldehyde, 4- tert- butylbenzaldehyde, 4-methylbenzaldehyde, 4-chlorobenzaldehyde, 4-fluorobenzaldehyde, 2,4-difluorobenzaldehyde, 4-methoxybenzaldehyde, and 1-butanal did not provide the corresponding products under the investigated conditions. In these reactions, polar dark-brown materials were obtained, likely due to polymerization of enynes.
    • Reactions with aldehydes, such as benzaldehyde, 4- tert- butylbenzaldehyde, 4-methylbenzaldehyde, 4-chlorobenzaldehyde, 4-fluorobenzaldehyde, 2,4-difluorobenzaldehyde, 4-methoxybenzaldehyde, and 1-butanal did not provide the corresponding products under the investigated conditions. In these reactions, polar dark-brown materials were obtained, likely due to polymerization of enynes.
  • 40
    • 79955636249 scopus 로고    scopus 로고
    • See the Supporting Information for spectroscopic assignment and X-ray data for compound 4a (The crystallographic coordinates have been deposited with the Cambridge Crystallographic Data Centre; deposition no. 818904. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Rd., Cambridge CB2 1EZ, UK or via www.ccdc.cam.ac.uk/conts/retrieving. html).
    • See the Supporting Information for spectroscopic assignment and X-ray data for compound 4a (The crystallographic coordinates have been deposited with the Cambridge Crystallographic Data Centre; deposition no. 818904. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Rd., Cambridge CB2 1EZ, UK or via www.ccdc.cam.ac.uk/conts/retrieving. html).
  • 41
    • 79955617188 scopus 로고    scopus 로고
    • Gaussian 09 program, see the Supporting Information (SI) for the full citation.
    • Gaussian 09 program, see the Supporting Information (SI) for the full citation.


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