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Volumn 63, Issue 17, 1998, Pages 5919-5928

Lewis Acid-Promoted [2 + 1] Cycloaddition Reactions of a 1-Seleno-2-silylethene to 2-Phosphonoacrylates: Stereoselective Synthesis of a Novel Functionalized α-Aminocyclopropanephosphonic Acid

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EID: 0000989912     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9805450     Document Type: Article
Times cited : (46)

References (75)
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    • 11 The stereochemistry of 4 was assigned as E (ca. 90%>). See: (a) Reetz, M. T.; Peter, R.; von Itzstein, M. Chem. Ber. 1987, 720, 121. (b) Sainz-Díaz, C. I.; Gálvez-Ruano, E.; Hernández-Laguna, A.; Bellanato, J. J. Org. Chem. 1995, 60, 74.
    • (1987) Chem. Ber. , vol.720 , pp. 121
    • Reetz, M.T.1    Peter, R.2    Von Itzstein, M.3
  • 44
    • 85034478470 scopus 로고    scopus 로고
    • note
    • 6b.
  • 52
    • 85034463486 scopus 로고    scopus 로고
    • note
    • The geometries of P=O-monocoordinated and C=O-monocoordinated complexes, B and C, were also optimized, but these species were found to be much less stable than A (Figure 2) (in the structure below, energies in square brackets were obtained by ab initio RHF/ LANL2MB calculations and are relative ones to that of the complex A). (Matrix Presented)
  • 53
  • 55
    • 0029945591 scopus 로고    scopus 로고
    • 2-monocoordination to the phosphoryl oxygen of a ketovinylphosphonate was reported and the chemical shift change Δδ was +1.8 ppm. McClure C. K.; Hansen, K. B. Tetrahedron Lett. 1996, 37, 2149.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 2149
    • McClure, C.K.1    Hansen, K.B.2
  • 62
    • 85034485712 scopus 로고    scopus 로고
    • note
    • 4 complex shown below is 8.7 kcal/mol more unstable than the s-cis isomer by STO-3G//LANL2MB. Therefore, the s-cis isomer is probably the actual electrophile in this reaction. (Matrix Presented)
  • 70
    • 0029080647 scopus 로고
    • The synthesis of 3-methyl-and 3,3-dimethylphosphonocyclopropane lactone derivatives was recently reported. Using this method, only trace amounts of 3-unsubstituted derivatives could be obtained. These 3-substituted phosphonocyclopropane lactone derivatives are also promising precursors for 1-aminocyclopropanephosphonic acid derivatives by using the transformations described herein. Töke, L.; Jászay, Z. M.; Petneházy. I.; Clemetis, G.; Vereczkey, G. D.; Kövesdi, I.; Rockenbauer, A.; Kováts, K. Tetrahedron 1995, 51, 9167.
    • (1995) Tetrahedron , vol.51 , pp. 9167
    • Töke, L.1    Jászay, Z.M.2    Petneházy, I.3    Clemetis, G.4    Vereczkey, G.D.5    Kövesdi, I.6    Rockenbauer, A.7    Kováts, K.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.