Michael addition of N- and O-centred nucleophiles to tethered acrylates. The role of double bond geometry in controlling the diastereoselectivity of cyclisations leading to 2,6-disubstituted tetrahydropyrans and piperidines

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 10, 1996, Pages 967-969

  Banwell, Martin G ^a   Bui, Chinh T ^b   Pham, Ha T T ^b   Simpson, Gregory W ^c  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b UNIVERSITY OF MELBOURNE   (Australia)

^c CSIRO   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542421110     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960000967     Document Type: Article

References (13)

1. M. J. Munchhof andA. I. Meyers, J. Am. Chem. Soc., 1995, 117, 5399 and references cited therein.
2. T. L. B. Boivin, Tetrahedron, 1987, 43, 3309 and references cited therein.
3. Martin and co-workers (J. M. Palázon, M. A. Soler, M. A. Ramirez and V. S. Martin, Tetrahedron Lett., 1993, 34, 5467 and references cited therein) have reported on the use of intra-molecular Michael addition for the preparation of 2,3-disubstituted tetrahydropyrans.
4. Mandai et al. (T. Mandai, M. Ueda, K. Kashiwagi, M. Kawada and J. Tsuji, Tetrahedron Lett., 1993, 34, 111) have described the intramolecular 1,4-addition of oxyanions to tethered α,β-unsaturated sulfoxides as a method for preparing, in a diastereoselective fashion, 2,6-disubstituted tetrahydropyrans.
5. Machinaga and Kibayashi (N. Machinaga and C. Kibayashi, Tetrahedron Lett., 1993, 34, 5739) have exploited the title reaction as a key step in a synthesis of (+)-decarestrictine L (a 2,3,6-trisubstituted tetrahydropyran) but did not examine the impact of double bond geometry on the diastereoselectivity of the cyclisation process.
6. For an example of a related reaction involving a nitrogen-centred nucleophile see S. Knapp and J. J. Hale, J. Org. Chem., 1993, 58, 2650.
7. R. Grigg, J. Markandu, T. Perrior, S. Surendrakumar and W. J. Warnock, Tetrahedron, 1992, 48, 6929.
8. W. C. Still and C. Gennari, Tetrahedron Lett., 1983, 24, 4405.
9. B. Maurer, A. Grieder and W. Thommen, Helv. Chim. Acta, 1979, 62, 44.
10. P. Varelis, A. J. Graham, B. L. Johnson, B. W. Skelton and A. H. White, Amt. J. Chem., 1994, 47, 1735 and references cited therein.
11. O. Muraoka, M. Okumura, T. Maeda, L. Wang and G. Tanabe, Chem. Pharm. Bull., 1995, 43, 517 and references cited therein.
12. 6 and two subsequent syntheses of compound 11 (F. W. Lichtenthaler, F. D. Klinger and P. Jarglis, Carbohydr. Res., 1984, 132, C1;
13. V. Ragoussis and V. Theodorou, Synthesis, 1993, 84) intramolecular Michael addition of an oxyanion to a tethered acrylate was employed as the key step. However, in none of these cases was it possible to determine the impact of double-bond geometry on the diastereoselectivity of the cyclisation reaction.