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Volumn 11, Issue 13, 2009, Pages 2776-2779

Catalytic generation of cesium acetylide by CsF: Synthesis of 1,3-benzothiazines from cyclic sulfenamide

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EID: 67649503037     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9009333     Document Type: Article
Times cited : (28)

References (40)
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    • Tejedor, D.; López-Tosco, S.; Cruz-Acosta, F.; Garcia-Tellado, F.; Méndez-Abt, G.; Garcia-Tellado, F. Angew. Chem., Int. Ed. 2009, 48, 20902098.
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    • For reviews, see: a
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    • Tzalis, D.; Knochel, P. Angew. Chem., Int. Ed. 1999, 38, 14631465.
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    • Highly enantioselective alkynylations have been described recently but required the use of a large excess of zinc derivative
    • Highly enantioselective alkynylations have been described recently but required the use of a large excess of zinc derivative:
  • 15
    • 22144446027 scopus 로고    scopus 로고
    • Surprisingly, no reaction, occurred when zinc acetylide ester was added on imine
    • (f) Cozzi, P. G.; Rudolph, J.; BoIm, C.; Norrby, P.-O.; Tomasini, C. J. Org. Chem. 2005, 70, 5733-5736. Surprisingly, no reaction, occurred when zinc acetylide ester was added on imine.
    • (2005) J. Org. Chem , vol.70 , pp. 5733-5736
    • Cozzi, P.G.1    Rudolph, J.2    BoIm, C.3    Norrby, P.-O.4    Tomasini, C.5
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    • Reviews on sulfanamides: (a) Davis, F. A. Int. J. Sulfur Chem. 1973, 8, 71-81.
    • (1973) Int. J. Sulfur Chem , vol.8 , pp. 71-81
    • Davis, F.A.1
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    • Reactivity of sulfenamides with acetylides
    • (b) Craine, L.; Raban, M. Chem. Rev. 1989, 89, 689-712. Reactivity of sulfenamides with acetylides
    • (1989) Chem. Rev , vol.89 , pp. 689-712
    • Craine, L.1    Raban, M.2
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    • Naito, H.; Hâta, T.; Urabe, H. Tetrahedron Lett. 2008, 49, 22982301.
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    • Alkyl N-Boc-imines were prepared in-situ from corresponding sulfones by an excess of ortho-lithiated sulfoxide (2.1 equiv): Grach, G.; Sopkova-de Oliveira Santos, J.; Lohier, J.-F.; Mojovic, L.; Pié, N.; Turck, A.; Reboul, V.; Metzner, P. J. Org. Chem. 2006, 71, 9572-9579.
    • Alkyl N-Boc-imines were prepared in-situ from corresponding sulfones by an excess of ortho-lithiated sulfoxide (2.1 equiv): Grach, G.; Sopkova-de Oliveira Santos, J.; Lohier, J.-F.; Mojovic, L.; Pié, N.; Turck, A.; Reboul, V.; Metzner, P. J. Org. Chem. 2006, 71, 9572-9579.
  • 34
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    • The chemical shift of vinylic proton are consistent for each diastereoisomer: 6.35-6.44 ppm. for major and 5.79-5.93 ppm. for minor.
    • The chemical shift of vinylic proton are consistent for each diastereoisomer: 6.35-6.44 ppm. for major and 5.79-5.93 ppm. for minor.
  • 35
    • 33947706661 scopus 로고    scopus 로고
    • To the best of our knowledge, only corresponding lithium acetylide has been described: Jones, A. C.; Sanders, A. W.; Bevan, M. J.; Reich, H. J. J. Am. Chem. Soc. 2007, 129, 3492-3493.
    • To the best of our knowledge, only corresponding lithium acetylide has been described: Jones, A. C.; Sanders, A. W.; Bevan, M. J.; Reich, H. J. J. Am. Chem. Soc. 2007, 129, 3492-3493.
  • 36
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    • The chemical shift of the vinylic proton are consistent with the diastereoisomer E as the major isomer: 6.23-6.33 ppm.
    • The chemical shift of the vinylic proton are consistent with the diastereoisomer E as the major isomer: 6.23-6.33 ppm.
  • 38
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    • These compounds are analogous to benzothiazinone described as heart muscular cell apoptosis inhibitors and cell death inhibitor
    • These compounds are analogous to benzothiazinone described as heart muscular cell apoptosis inhibitors and cell death inhibitor.


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