Highly diastereoselective conjugate addition of carbon nucleophiles to a chiral oxygenated α,β-unsaturated α-lactone. A straightforward synthesis of functionalized branched-chain L-sugars

Journal of Organic Chemistry

Volumn 61, Issue 3, 1996, Pages 1143-1147

  Herradón, Bernardo ^a   Fenude, Emma ^b   Bao, Rong ^a   Valverde, Serafín ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001089088     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9514836     Document Type: Article

References (41)

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17. To the best of our knowledge, the only reported example of stereocontrolled conjugate addition of carbon nucleophiles to this kind of molecules is the addition of a benzyllithium reagent to an oxygenated α,β-unsaturated δ-lactone as a step in the synthesis of olivin trimethyl ether; see: Franck, R. W.; Bhat, V.; Subramanian, C. S. J. Am. Chem. Soc. 1986, 108, 2455-2457. On the other hand, the conjugate addition to α,β-unsaturated γ-lactones and alkyl-substituted α,β-unsaturated δ-lactones have been more extensively studied; for a survey of the literature, see pp 283-297 in ref 3c.
18. Herradón, B. Ph. D. Dissertation, Universidad Complutense, Madrid, 1986. García-Ochoa, S. Ph. D. Dissertation, Universidad Autónoma, Madrid, 1988.
19. Herradón, B. Ph. D. Dissertation, Universidad Complutense, Madrid, 1986. García-Ochoa, S. Ph. D. Dissertation, Universidad Autónoma, Madrid, 1988.
20. The lack of stereocontrol in the intermolecular reaction must be due to partial epimerization of the initially formed product through a retro-Michael addition.
21. (a) For recent syntheses of L-sugars, see: Ford, M. J.; Ley, S. V. Synlett 1990, 771-772. Giuliano, R. M.; Villani, F. J., Jr J. Org. Chem. 1995, 60, 202-211
22. (a) For recent syntheses of L-sugars, see: Ford, M. J.; Ley, S. V. Synlett 1990, 771-772. Giuliano, R. M.; Villani, F. J., Jr J. Org. Chem. 1995, 60, 202-211
23. (b) For recent syntheses of branched-chain sugars, see: Toshima, K.; Yoshida, T ; Mukaiyama, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 4139-4142. Yanagihara, R.; Osanai, S.; Yoshikawa, S. Chem. Lett. 1992, 89-90.
24. (b) For recent syntheses of branched-chain sugars, see: Toshima, K.; Yoshida, T ; Mukaiyama, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 4139-4142. Yanagihara, R.; Osanai, S.; Yoshikawa, S. Chem. Lett. 1992, 89-90.
25. (c) For a review of earlier work, see: McGarvey, G. J., Kimura, M.; Oh, T., Williams, J. M. J Carbohydr. Chem. 1984, 3, 125-188.
26. 13C-NMR spectra.
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31. 1H-NMR evidence).
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33. Herradón, B.; Fenude, E. Manuscript in preparation. See also: Liskamp, R. M. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 305-307.
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36. Very preliminary results on the conjugate addition to the lactones 9 and 10 (see Chart 1) seem to indicate that stereoelectronic factors are more important than steric influences in determining the stereochemical outcome of the Michael addition of dialkyl cuprates. Sánchez-Sancho, F.; Herradón, B. Manuscript in preparation.
37. The epimer of 11a (namely, 12) is expected to have the conformation indicated below, where H-4 is axially oriented. (Matrix Presented)
38. t to generate the carbanion, following a procedure analogous to the reported in the Experimental Section for the conjugate addition of active methylene compounds.
39. For a general experimental procedure, see: Herradón, B.; Valverde, S. Tetrahedron: Asymmetry 1994, 5, 1479-1500.
40. 2Li (1.0 M) in pentane, and 1.0 M vinylmagnesium bromide in THF were used for generating the copper reagent.
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