C-O versus C-C Tandem Cycloalkylation of Stabilized Carbanions. Facile One-Pot Stereoselective Preparation of Functionalized Cyclic Enol Ethers

Synlett

Volumn 1996, Issue 4, 1996, Pages 339-340

  Lavoisier, Tania ^a   Rodriguez, Jean ^a  

^a UMR au CNRS 6516   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002631382     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5415     Document Type: Article

References (22)

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2. Lavoisier, T.; Rodriguez, J. Synlett 1995, 1241.
3. Baldwin, J. E.; Kruse, L. I. J. Chem. Soc., Chem. Commun. 1977, 233.
4. For a recent fused dihydrofuran synthesis via the intramolecular Mitsunobu reaction, see: Tenaglia, A.; Le Brazidec, J.-Y.; Souchon, F. Tetrahedron Lett. 1995, 36, 4241.
5. While this work was underway a similar approach concerning the reactivity of α-substituted cyclohexanone anions with cis- or trans-1,4-dibromo-2-butene has been reported: Wang, T.; Chen, J.; Zhao, K. J. Org. Chem. 1995, 60, 2668.
6. For a review on synthetic routes to tetrahydrofurans, see: Boivin, T. L. B. Tetrahedron 1987, 43, 3309.
7. Rhoads, S. J.; Brandenburg, C. F. J. Am. Chem. Soc. 1966, 88, 4294.
8. Tsuji, J.; Kobayashi, Y.; Kataoka, H.; Takahashi, T. Tetrahedron Lett. 1980, 21, 1475. Trost, B. M.; Runge, T.A. J. Am. Chem. Soc. 1981, 103, 7550 and 7559.
9. Tsuji, J.; Kobayashi, Y.; Kataoka, H.; Takahashi, T. Tetrahedron Lett. 1980, 21, 1475. Trost, B. M.; Runge, T.A. J. Am. Chem. Soc. 1981, 103, 7550 and 7559.
10. Nemoto, H. Tetrahedron Lett. 1994, 35, 7785. Lygo, B. Tetrahedron 1988, 44, 6889.
11. Nemoto, H. Tetrahedron Lett. 1994, 35, 7785. Lygo, B. Tetrahedron 1988, 44, 6889.
12. Wang, T.; Hong, F., Zhao, K. Tetrahedron Lett. 1995, 36, 6407. Wang, T., Chen, J.; Landrey, D. W.; Zhao, K. Synlett 1995, 543.
13. Wang, T.; Hong, F., Zhao, K. Tetrahedron Lett. 1995, 36, 6407. Wang, T., Chen, J.; Landrey, D. W.; Zhao, K. Synlett 1995, 543.
14. For preparation of related enol ethers using dianion chemistry, see inter alia: Bryson, T. A. J. Org. Chem. 1973, 38, 3428. Lygo, B.; O'Connor, N.; Wilson, P. R. Tetrahedron 1988, 44, 6881.
15. For preparation of related enol ethers using dianion chemistry, see inter alia: Bryson, T. A. J. Org. Chem. 1973, 38, 3428. Lygo, B.; O'Connor, N.; Wilson, P. R. Tetrahedron 1988, 44, 6881.
16. 2O/pentane).
17. Lavoisier, T., PhD Thesis, University of Marseille, in progress.
18. Although the dianion chemistry has been extensively studied, to our knowledge such α,α'-ketodianions have not yet been used for this purpose: Thompson, C. M. Dianion Chemistry in Organic Synthesis, CRC Press Inc., Boca Raton 1994.
19. Bahurel, Y.; Collonges, F.; Menet, A.; Pautet, F.; Poncet, A.; Descotes, G.; Bull. Soc. Chem. Fr. 1971, 2203.
20. Deprés, J.-P.; Greene, A. E. J. Org. Chem. 1984, 49, 928. However it is known that, using palladium chemistry, the anions derived from acetoacetates and even from dimethyl 1,3-acetonedicarboxylate condense respectively with cis-2-butylene dicarbonates and cis-1,4-cycloalkenediol derivatives to furnish vinyldihydrofurans: Hayashi, T.; Yamamoto, A.; Ito, Y. Tetrahedron Lett. 1988, 29, 669. Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016.
21. Deprés, J.-P.; Greene, A. E. J. Org. Chem. 1984, 49, 928. However it is known that, using palladium chemistry, the anions derived from acetoacetates and even from dimethyl 1,3-acetonedicarboxylate condense respectively with cis-2-butylene dicarbonates and cis-1,4-cycloalkenediol derivatives to furnish vinyldihydrofurans: Hayashi, T.; Yamamoto, A.; Ito, Y. Tetrahedron Lett. 1988, 29, 669. Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016.
22. Deprés, J.-P.; Greene, A. E. J. Org. Chem. 1984, 49, 928. However it is known that, using palladium chemistry, the anions derived from acetoacetates and even from dimethyl 1,3-acetonedicarboxylate condense respectively with cis-2-butylene dicarbonates and cis-1,4-cycloalkenediol derivatives to furnish vinyldihydrofurans: Hayashi, T.; Yamamoto, A.; Ito, Y. Tetrahedron Lett. 1988, 29, 669. Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016.