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Volumn , Issue 9, 2008, Pages 1575-1581

Synthesis of novel bis(β-lactam)-1,3-diynes by copper-promoted homo- or cross-coupling of alkynyl-2-azetidinones

Author keywords

Alkynes; C C coupling; Copper; Lactams; Synthetic methods

Indexed keywords


EID: 53849097713     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200701083     Document Type: Article
Times cited : (14)

References (68)
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    • M. I. Page (Ed.), The Chemistry of β-Lactams, Chapman and Hall, London, 1992.
    • c) M. I. Page (Ed.), The Chemistry of β-Lactams, Chapman and Hall, London, 1992.
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    • For recent selected examples for the homocoupling of alkynes, see: a
    • For recent selected examples for the homocoupling of alkynes, see: a) B. J. Morgan, X. Xie, P.-W. Phuan, M. C. Kozlowski, J. Org. Chem. 2007, 72, 6171;
    • (2007) J. Org. Chem , vol.72 , pp. 6171
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    • For recent selected references on heterocoupling alkyne reactions, see: k
    • For recent selected references on heterocoupling alkyne reactions, see: k) J. P. Marino, H. N. Nguyen, J. Org. Chem. 2002, 67, 6841;
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    • Marino, J.P.1    Nguyen, H.N.2
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    • Angew. Chem. 2007, 119, 6804;
    • (2007) Angew. Chem , vol.119 , pp. 6804
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    • Angew. Chem. 2006, 118, 4613;
    • (2006) Angew. Chem , vol.118 , pp. 4613
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    • 2-Symmetrical compound (+)-2a can be considered as a hybrid scaffold as a combination of the naturally occurring β-lactam and 1,3-diyne moieties. For a review on natural product hybrids, see: a) L. F. Tietze, H. P. Bell, S. Chandrasekhar, Angew. Chem. Int. Ed. 2003, 42, 3996.
    • 2-Symmetrical compound (+)-2a can be considered as a hybrid scaffold as a combination of the naturally occurring β-lactam and 1,3-diyne moieties. For a review on natural product hybrids, see: a) L. F. Tietze, H. P. Bell, S. Chandrasekhar, Angew. Chem. Int. Ed. 2003, 42, 3996.
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    • 2-symmetrical natural products, see: b M. Vrettou, A. A. Gray, A. R. E. Brewer, A. G. M. Barrett, Tetrahedron 2007, 63, 1487.
    • 2-symmetrical natural products, see: b) M. Vrettou, A. A. Gray, A. R. E. Brewer, A. G. M. Barrett, Tetrahedron 2007, 63, 1487.
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    • 53849149316 scopus 로고    scopus 로고
    • In addition to being odorless, K2CO3 can be easily removed by aqueous workup. To the best of our knowledge, this is the first time that K2CO3 has been used for the dimerization of terminal alkynes
    • 3 has been used for the dimerization of terminal alkynes.
  • 58
    • 33645499678 scopus 로고    scopus 로고
    • Unsymmetrical diynes play an important structural role in many natural products and possess a wide range of potential applications in material science. For selected natural products references, see: a S. López, F. Fernández-Trillo, P. Midón, L. Castedo, C. Saá, J. Org. Chem. 2006, 71, 2802;
    • Unsymmetrical diynes play an important structural role in many natural products and possess a wide range of potential applications in material science. For selected natural products references, see: a) S. López, F. Fernández-Trillo, P. Midón, L. Castedo, C. Saá, J. Org. Chem. 2006, 71, 2802;
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    • For selected material science references, see: f
    • For selected material science references, see: f) X. Nie, G. Wang, J. Org. Chem. 2006, 71, 4734;
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    • Nie, X.1    Wang, G.2
  • 68
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    • 1H NMR spectra. The assignment of relative stereochemistry on the basis of the observed coupling constant for methine protons 3-H and 4-H is a very well-established criterion in β-lactam chemistry. See, for example: B. Alcaide, P. Almendros, N. R. Salgado, A. Rodríguez-Vicente, J. Org. Chem. 2000, 65, 4453.
    • 1H NMR spectra. The assignment of relative stereochemistry on the basis of the observed coupling constant for methine protons 3-H and 4-H is a very well-established criterion in β-lactam chemistry. See, for example: B. Alcaide, P. Almendros, N. R. Salgado, A. Rodríguez-Vicente, J. Org. Chem. 2000, 65, 4453.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.