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Volumn , Issue 8, 2006, Pages 844-846

Regioselective and enantiospecific rhodium-catalyzed allylic amination with thymine: Synthesis of a new conformationally rigid nucleoside

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; NUCLEOSIDE; RADICAL; RHODIUM; THYMINE;

EID: 32844468527     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b513083b     Document Type: Article
Times cited : (27)

References (31)
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  • 2
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    • and pertinent references therein
    • For a review on allylic animation, see: M. Johannsen and K. A. Jørgensen, Chem. Rev., 1998, 98, 1689 and pertinent references therein.
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  • 3
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    • and pertinent references cited therein
    • For a recent perspective of asymmetric allylic substitution, in which nucleosides are utilized as nucleophiles, see: B. M. Trost, J. Org. Chem., 2004, 69, 5813 and pertinent references cited therein.
    • (2004) J. Org. Chem. , vol.69 , pp. 5813
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  • 4
    • 0003692824 scopus 로고
    • For an example of the challenges associated with controlling regioselectivity in the metal-catalyzed allylic amination of unsymmetrical allylic alcohol derivatives using nucleosides, see: M. L. Falck-Pedersen, T. Benneche and K. Undheim, Acta Chem. Scand., 1989, 43, 251.
    • (1989) Acta Chem. Scand. , vol.43 , pp. 251
    • Falck-Pedersen, M.L.1    Benneche, T.2    Undheim, K.3
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    • ed. P. A. Evans, Wiley-VCH, Weinheim, ch. 10, and pertinent references cited therein
    • For a recent review of the rhodium-catalyzed allylic substitution reaction, see: D. K. Leahy and P. A. Evans, in Modern Rhodium-Catalyzed Organic Reactions, ed. P. A. Evans, Wiley-VCH, Weinheim, 2005, ch. 10, p. 191 and pertinent references cited therein.
    • (2005) Modern Rhodium-Catalyzed Organic Reactions , pp. 191
    • Leahy, D.K.1    Evans, P.A.2
  • 12
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    • note
    • The attempted allylic amination reaction with the lithium anion of thymine gave a complex mixture of products, thereby illustrating the importance of the protecting group.
  • 13
    • 32844456102 scopus 로고    scopus 로고
    • note
    • 1 = H; 65.1 mg, 98%) as a colorless oil.
  • 17
    • 32844473550 scopus 로고    scopus 로고
    • note
    • 3-benzoyl thymine.
  • 18
    • 0000432226 scopus 로고    scopus 로고
    • ed. I. Ojima, Wiley-VCH, New York, 2nd edn, ch. 6
    • For a review of catalytic asymmetric dihydroxylation, see: R. A. Johnson and K. B. Sharpless, in Catalytic Asymmetric Synthesis, ed. I. Ojima, Wiley-VCH, New York, 2nd edn, 2000, ch. 6, p. 357.
    • (2000) Catalytic Asymmetric Synthesis , pp. 357
    • Johnson, R.A.1    Sharpless, K.B.2
  • 19
    • 0028605353 scopus 로고
    • For an example of improved enantioselectivity in the asymmetric dihydroxylation due to π-stacking, see: E. J. Corey, A. Guzman-Perez and M. C. Noe, J. Am. Chem. Soc., 1994, 116, 12109.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 12109
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  • 21
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    • For reviews on the Mitsunobu reaction, see: (a) O. Mitsunobu, Synthesis, 1981, 1;
    • (1981) Synthesis , pp. 1
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  • 24
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    • For a related example of a stereoselective free radical cyclization where a similar non-bonding interaction is invoked to rationalize the trans-diastereoselectivity, see: (a) D. J. Hart and K. Kanai, J. Am. Chem. Soc., 1983, 105, 1255;
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 1255
    • Hart, D.J.1    Kanai, K.2
  • 30
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    • For a related free radical reduction in a related thymine derivative, see: D. J. Fenick and D. E. Falvey, J. Org. Chem., 1994, 59, 4791.
    • (1994) J. Org. Chem. , vol.59 , pp. 4791
    • Fenick, D.J.1    Falvey, D.E.2
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    • note
    • The desired product was also obtained with a minor amount of the product from the epimerization of the methyl group (≤5%).


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