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Volumn 61, Issue 19, 1996, Pages 6735-6738

Bis-allylic templates for Pd(0)-catalyzed solid phase synthesis of tertiary amines

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EID: 0000141965     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960756+     Document Type: Article
Times cited : (27)

References (56)
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    • For reviews, see: (a) Heck, R. F. Palladium Reagents in Organic Chemistry; Academic Press: London, 1985. (b) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173-1192. (c) Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Pergamon Press: Oxford, 1982; Vol. 8, p 799. (d) Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: Berlin, 1981. (e) Trost, B. M. Acc. Chem. Res. 1980, 13, 385-393. (f) Trost, B. M. Pure Appl. Chem. 1981, 53, 2357-2370. (g) Eichelmann, H.; Gais, H. J. Tetrahedron: Asymmetry 1995, 6, 643-646. (h) Safi, M.; Sinou, D. Tetrahedron Lett. 1991, 32, 2025-2028. (i) Minami, I.; Ohashi, Y.; Shimizu, I.; Tsuji, J. Tetrahedron Lett. 1982, 23, 4809-4812. (j) Guibe, F.; Saint M. Leux, Y. Tetrahedron Lett. 1981, 22, 3591-3594.
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    • Minami, I.1    Ohashi, Y.2    Shimizu, I.3    Tsuji, J.4
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    • 0000282382 scopus 로고
    • For reviews, see: (a) Heck, R. F. Palladium Reagents in Organic Chemistry; Academic Press: London, 1985. (b) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173-1192. (c) Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Pergamon Press: Oxford, 1982; Vol. 8, p 799. (d) Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: Berlin, 1981. (e) Trost, B. M. Acc. Chem. Res. 1980, 13, 385-393. (f) Trost, B. M. Pure Appl. Chem. 1981, 53, 2357-2370. (g) Eichelmann, H.; Gais, H. J. Tetrahedron: Asymmetry 1995, 6, 643-646. (h) Safi, M.; Sinou, D. Tetrahedron Lett. 1991, 32, 2025-2028. (i) Minami, I.; Ohashi, Y.; Shimizu, I.; Tsuji, J. Tetrahedron Lett. 1982, 23, 4809-4812. (j) Guibe, F.; Saint M. Leux, Y. Tetrahedron Lett. 1981, 22, 3591-3594.
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  • 50
    • 85033842883 scopus 로고    scopus 로고
    • note
    • 4 caused by its air and moisture sensitivity.
  • 51
    • 85033841428 scopus 로고    scopus 로고
    • note
    • When the reaction was carried out in the absence of acetic acid, an appreciable amount of the (((3-hydroxy-2-methylenepropyl)oxy)-carbonyl)-N-benzylglycine was obtained.
  • 52
    • 85033867596 scopus 로고    scopus 로고
    • note
    • 19F NMR spectra of N-(4-fluorobenzyl)-N-(3-(tetrahydroisoquinolino)-2-methylenepropyl)glycine and N-(4-fluorobenzyl)-N-(benzylamino)-2-methylenepropyl)glycine revealed the stoichiometry corresponding to bis-trifluoroacetates after the preparative HPLC. Isolated yields are therefore based on stoichiometric amounts of trifluoroacetic acid per amine functionality.
  • 53
    • 85033870462 scopus 로고    scopus 로고
    • note
    • The purities of compounds 6, 7a-1 were calculated from integrated peak areas recorded by the HPLC analysis (215 nm) of the crude product which was cleaved from the solid support after complete conversion of the starting material.
  • 56
    • 85033836461 scopus 로고    scopus 로고
    • note
    • 2-allylic protons.


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