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Volumn , Issue 14, 2002, Pages 1945-1952

Asymmetric Michael addition of chiral lithiated sulfonates to nitroalkenes: Diastereo- and enantioselective synthesis of α,β-disubstituted γ-nitro and β-alkoxycarbonyl methyl sulfonates

Author keywords

Carbohydrates; Chiral auxiliaries; Meyer reaction; Michael additions; Nitroalkenes; Sulfonates

Indexed keywords

ORGANIC COMPOUNDS;

EID: 0036401809     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34368     Document Type: Article
Times cited : (27)

References (30)
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    • For general reviews on asymmetric Michael additions, see: (a) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771. (b) Yamamoto, Y.; Pyne, S. G.; Schinzer, D.; Feringa, B. L.; Jansen, J. F. G. A. In Houben Weyl, 4th Ed. Vol. E21b; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1995, Chap. 1.5.2;. (c) Leonard, J.; Diez-Barra, E.; Merino, S. Eur. J. Org. Chem. 1998, 2051.
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    • and literature cited therein
    • For some recent examples, see: (a) Schäfer, H.; Seebach, D. Tetrahedron 1995, 51, 2305. (b) Enders, D.; Otten, T. Synlett 1999, 747; and literature cited therein. (c) Enders, D.; Teschner, P.; Raabe, G. Synlett 2000, 637. (d) Enders, D.; Tedeschi, L.; Bats, J. W. Angew. Chem. Int. Ed. 2000, 39, 4605; Angew. Chem. 2000, 112, 4774.
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    • For some recent examples, see: (a) Schäfer, H.; Seebach, D. Tetrahedron 1995, 51, 2305. (b) Enders, D.; Otten, T. Synlett 1999, 747; and literature cited therein. (c) Enders, D.; Teschner, P.; Raabe, G. Synlett 2000, 637. (d) Enders, D.; Tedeschi, L.; Bats, J. W. Angew. Chem. Int. Ed. 2000, 39, 4605; Angew. Chem. 2000, 112, 4774.
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    • For some recent examples, see: (a) Schäfer, H.; Seebach, D. Tetrahedron 1995, 51, 2305. (b) Enders, D.; Otten, T. Synlett 1999, 747; and literature cited therein. (c) Enders, D.; Teschner, P.; Raabe, G. Synlett 2000, 637. (d) Enders, D.; Tedeschi, L.; Bats, J. W. Angew. Chem. Int. Ed. 2000, 39, 4605; Angew. Chem. 2000, 112, 4774.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 4605
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    • For some recent examples, see: (a) Schäfer, H.; Seebach, D. Tetrahedron 1995, 51, 2305. (b) Enders, D.; Otten, T. Synlett 1999, 747; and literature cited therein. (c) Enders, D.; Teschner, P.; Raabe, G. Synlett 2000, 637. (d) Enders, D.; Tedeschi, L.; Bats, J. W. Angew. Chem. Int. Ed. 2000, 39, 4605; Angew. Chem. 2000, 112, 4774.
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    • note
    • The experimental data will be reported in a separate full paper on the α-alkylations.
  • 25
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    • For representative syntheses of the sodium sulfonates, see: (a) Otto, S.; Engberts, J. B. F. N.; Kwak, J. C. T. J. Am. Chem. Soc. 1998, 120, 9517. (b) Abdellaoui, H.; Depreux, P.; Lesieur, D.; Pfeiffer, B.; Bontempelli, P. Synth. Commun. 1995, 25, 1303.
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