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Volumn 52, Issue 22, 1987, Pages 4984-4993

Selective Cleavage of the Allyl and Allyloxycarbonyl Groups through Palladium-Catalyzed Hydrostannolysis with Tributyltin Hydride. Application to the Selective Protection-Deprotection of Amino Acid Derivatives and in Peptide Synthesis

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EID: 33845282500     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00231a027     Document Type: Article
Times cited : (247)

References (50)
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    • Stewart, J. M.; Young, J. D. Solid Phase Peptide Synthesis, 2nd ed.; Pierce Chemical Company: Rockford, IL, 1984. Merifield, R. B. Angew. Chem., Int. Ed. Engl. 1985, 24, 799. An orthogonal system is
    • Barany, G.; Albericio, F. J. Am. Chem. Soc. 1985, 107, 4936. Stewart, J. M.; Young, J. D. Solid Phase Peptide Synthesis, 2nd ed.; Pierce Chemical Company: Rockford, IL, 1984. Merifield, R. B. Angew. Chem., Int. Ed. Engl. 1985, 24, 799. An orthogonal system is
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 4936
    • Barany, G.1    Albericio, F.2
  • 21
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    • Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: Berlin, 1980; pp 125–132.
    • Trost, B. M. Acc. Chem. Res. 1980,13, 385. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: Berlin, 1980; pp 125–132.
    • (1980) Acc. Chem. Res. , vol.13 , pp. 385
    • Trost, B.M.1
  • 22
    • 0000470828 scopus 로고
    • deprotection of allyl carboxylates with Me2CuLi, see: Ho, T. L. Synth. Commun. 1978, 8, 15. Selective cleavage of allyl groups, especially of allyl
    • Corey, E. J.; Suggs, J. W. J. Org. Chem. 1973, 38, 3223. For deprotection of allyl carboxylates with Me2CuLi, see: Ho, T. L. Synth. Commun. 1978, 8, 15. Selective cleavage of allyl groups, especially of allyl
    • (1973) J. Org. Chem. , vol.38 , pp. 3223
    • Corey, E.J.1    Suggs, J.W.2
  • 23
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    • Boissonas, R. A.; Preitner, G. Helv. Chim. Acta 1953, 36, 875.
    • Stevens, C. M.; Watanabe, R. J. Am. Chem. Soc. 1950, 72, 725. Boissonas, R. A.; Preitner, G. Helv. Chim. Acta 1953, 36, 875.
    • (1950) J. Am. Chem. Soc. , vol.72 , pp. 725
    • Stevens, C.M.1    Watanabe, R.2
  • 24
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    • and references cited therein. Moreau, B.; Lavielle, S.; Marquet, A. Tetrahedron Lett. 1977,, 2591.
    • De Koning, J. H.; Van Boom, J. H. Synthesis 1981, 306 and references cited therein. Moreau, B.; Lavielle, S.; Marquet, A. Tetrahedron Lett. 1977,, 2591.
    • (1981) Synthesis , pp. 306
    • De Koning, J.H.1    Van Boom, J.H.2
  • 25
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    • Hartley, F. R. The Chemistry of Platinum and Palladium; Applied Science Publishers; London, 1973; pp 30–44.
    • Ugo, R. Coordination Chemistry Review, 1968, 3, 319, Hartley, F. R. The Chemistry of Platinum and Palladium; Applied Science Publishers; London, 1973; pp 30–44.
    • (1968) Coordination Chemistry Review , vol.3 , pp. 319
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  • 32
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    • Proceedings of the 14th European Peptide Symposium; Loffet, A., Ed.; Editions de Universite de Bruxelles: Brussels
    • Stewart, J. M. In Peptides 1976, Proceedings of the 14th European Peptide Symposium; Loffet, A., Ed.; Editions de l'Universite de Bruxelles: Brussels, 1977; p 285.
    • (1976) In Peptides , pp. 285
    • Stewart, J.M.1


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