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Volumn 130, Issue 12, 2008, Pages 4196-4201

Stereodivergent methodology for the synthesis of complex pyrrolidines

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; ENANTIOMERS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 41149174128     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja710289k     Document Type: Article
Times cited : (160)

References (70)
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    • For construction of the pyrrolidine motif via cyclopropanes, see: a
    • For construction of the pyrrolidine motif via cyclopropanes, see: (a) Danishefsky, S.; Regan, J.; Doehner, R. J. Org. Chem. 1981, 46, 5255-5261.
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    • For selected classical methods of pyrrolidine synthesis, see: a
    • For selected classical methods of pyrrolidine synthesis, see: (a) Wojcik, B.; Adkins, H. J. Am. Chem. Soc. 1934, 56, 2419-2424.
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    • and references therein. For anionic cyclization methods of pyrrolidine synthesis, see: h
    • For anionic cyclization methods of pyrrolidine synthesis, see: (h) Lorthiois, E.; Marek, I.; Normant, J. F. J. Org. Chem. 1998, 63, 2442-2450 and references therein.
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    • For cycloaddition strategies toward pyrrolidine synthesis, see: i
    • For cycloaddition strategies toward pyrrolidine synthesis, see: (i) Overman, L. E.; Kakimoto, M.-A. J. Am. Chem. Soc. 1979, 101, 1310-1312.
    • (1979) J. Am. Chem. Soc , vol.101 , pp. 1310-1312
    • Overman, L.E.1    Kakimoto, M.-A.2
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    • For seminal reports on the asymmetric 1,3-dipolar cycloaddition toward pyrrolidine synthesis, see: a
    • For seminal reports on the asymmetric 1,3-dipolar cycloaddition toward pyrrolidine synthesis, see: (a) Airway, P.; Grigg, R. Tetrahedron Lett. 1991, 32, 5817-5820.
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    • Airway, P.1    Grigg, R.2
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    • Maring, C.; McDaniel, K.; Krueger, A.; Zhao, C.; Sun, M.; Madigan, D.; DeGoey, D.; Chen, H.-J.; Yeung, M. C.; Flosi, W.; Grampovnik, D.; Kati, W.; Klein, L.; Stewart, K.; Stoll, V.; Saldivar, A.; Montgomery, D.; Carrick, R.; Steffy, K.; Kempf, D.; Molla, A.; Kohlbrenner, W.; Kennedy, A.; Herrin, T.; Xu, Y.; Laver, W. G. Presented at the 14th International Conference on Antiviral Research. Antiviral Res. 2001, 50, A76; Abstract 129.
    • Maring, C.; McDaniel, K.; Krueger, A.; Zhao, C.; Sun, M.; Madigan, D.; DeGoey, D.; Chen, H.-J.; Yeung, M. C.; Flosi, W.; Grampovnik, D.; Kati, W.; Klein, L.; Stewart, K.; Stoll, V.; Saldivar, A.; Montgomery, D.; Carrick, R.; Steffy, K.; Kempf, D.; Molla, A.; Kohlbrenner, W.; Kennedy, A.; Herrin, T.; Xu, Y.; Laver, W. G. Presented at the 14th International Conference on Antiviral Research. Antiviral Res. 2001, 50, A76; Abstract 129.
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    • For a review on the synthesis of 2,5-trans-pyrrolidines, see: Pichon, M.; Figadère, B. Tetrahedron: Asymmetry 1996, 7, 927-964.
    • For a review on the synthesis of 2,5-trans-pyrrolidines, see: Pichon, M.; Figadère, B. Tetrahedron: Asymmetry 1996, 7, 927-964.
  • 44
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    • For syntheses, see: c
    • For syntheses, see: (c) Kwon, S.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 16796-16797.
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    • Racemic 15 is easily prepared via hydroboration of readily available (+/-)-2-vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester. See Supporting Information.
    • Racemic 15 is easily prepared via hydroboration of readily available (+/-)-2-vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester. See Supporting Information.
  • 63
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    • This sequence is amenable to multigram scale, R-Butane triol is also commercially available
    • This sequence is amenable to multigram scale. (R)-Butane triol is also commercially available.
  • 64
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    • and ref 12d. For mechanistic insight on the related nitrone cycloaddition with cyclopropane diesters, see
    • For mechanistic insight on the related nitrone cycloaddition with cyclopropane diesters, see: Karadeolian, A.; Kerr, M. A. J. Org. Chem. 2007, 72, 10251-10253 and ref 12d.
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    • The cis-adducts underwent extensive decomposition upon attempted demethoxycarbonylation.
    • The cis-adducts underwent extensive decomposition upon attempted demethoxycarbonylation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.