A versatile preparation of α,β-unsaturated lactones from homoallylic alcohols

Organic Letters

Volumn 1, Issue 3, 1999, Pages 411-413

  Keck, Gary E ^a   Li, Xiang Yi ^a   Knutson, Chad E ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; ALLYL COMPOUND; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LACTONE; LITHIUM DERIVATIVE;

ARTICLE; CHEMISTRY; SYNTHESIS;

ALCOHOLS; ALDEHYDES; ALLYL COMPOUNDS; INDICATORS AND REAGENTS; LACTONES; LITHIUM COMPOUNDS;

EID: 0033549671     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990632u     Document Type: Article

References (19)

1. For a review on the use of allylmetals, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (a) Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G.; Livingston, A. B. J. Am. Chem. Soc. 1995, 117, 6619. (b) Keck, G. E.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265. Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927. Keck, G. E.; Abbott, D. E.; Wiley M. R. Tetrahedron Lett. 1987, 28, 139. (e) Keck, G. E.; Savin, K. A.; Cressman, E. N. K.; Abbott, D. E. J. Org. Chem. 1994, 59, 7889.
2. For a review on the use of allylmetals, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (a) Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G.; Livingston, A. B. J. Am. Chem. Soc. 1995, 117, 6619. (b) Keck, G. E.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265. Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927. Keck, G. E.; Abbott, D. E.; Wiley M. R. Tetrahedron Lett. 1987, 28, 139. (e) Keck, G. E.; Savin, K. A.; Cressman, E. N. K.; Abbott, D. E. J. Org. Chem. 1994, 59, 7889.
3. For a review on the use of allylmetals, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (a) Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G.; Livingston, A. B. J. Am. Chem. Soc. 1995, 117, 6619. (b) Keck, G. E.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265. Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927. Keck, G. E.; Abbott, D. E.; Wiley M. R. Tetrahedron Lett. 1987, 28, 139. (e) Keck, G. E.; Savin, K. A.; Cressman, E. N. K.; Abbott, D. E. J. Org. Chem. 1994, 59, 7889.
4. For a review on the use of allylmetals, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (a) Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G.; Livingston, A. B. J. Am. Chem. Soc. 1995, 117, 6619. (b) Keck, G. E.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265. Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927. Keck, G. E.; Abbott, D. E.; Wiley M. R. Tetrahedron Lett. 1987, 28, 139. (e) Keck, G. E.; Savin, K. A.; Cressman, E. N. K.; Abbott, D. E. J. Org. Chem. 1994, 59, 7889.
5. For a review on the use of allylmetals, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (a) Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G.; Livingston, A. B. J. Am. Chem. Soc. 1995, 117, 6619. (b) Keck, G. E.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265. Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927. Keck, G. E.; Abbott, D. E.; Wiley M. R. Tetrahedron Lett. 1987, 28, 139. (e) Keck, G. E.; Savin, K. A.; Cressman, E. N. K.; Abbott, D. E. J. Org. Chem. 1994, 59, 7889.
6. For a review on the use of allylmetals, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (a) Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G.; Livingston, A. B. J. Am. Chem. Soc. 1995, 117, 6619. (b) Keck, G. E.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265. Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927. Keck, G. E.; Abbott, D. E.; Wiley M. R. Tetrahedron Lett. 1987, 28, 139. (e) Keck, G. E.; Savin, K. A.; Cressman, E. N. K.; Abbott, D. E. J. Org. Chem. 1994, 59, 7889.
7. (a) Brown, H. C.; Vara Prasad, J. V. N.; Zee, S.-H. J. Org. Chem. 1986, 51, 432. (b) Corey, E. J.; Yu, C.-M.; Kim, S.-S. J. Am. Chem. Soc. 1989, 111, 5495. Roush, W. R.; Park, J. C. J. Org. Chem. 1990, 55, 1143. Hafner, A.; Duthaler, R. O.; Marti, R.; Rihs, G.; Rothe-Streit, P.; Scwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321. (e) Marshall, J. A.; Gung, W. Y. Tetrahedron 1989, 45, 1043.
8. (a) Brown, H. C.; Vara Prasad, J. V. N.; Zee, S.-H. J. Org. Chem. 1986, 51, 432. (b) Corey, E. J.; Yu, C.-M.; Kim, S.-S. J. Am. Chem. Soc. 1989, 111, 5495. Roush, W. R.; Park, J. C. J. Org. Chem. 1990, 55, 1143. Hafner, A.; Duthaler, R. O.; Marti, R.; Rihs, G.; Rothe-Streit, P.; Scwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321. (e) Marshall, J. A.; Gung, W. Y. Tetrahedron 1989, 45, 1043.
9. (a) Brown, H. C.; Vara Prasad, J. V. N.; Zee, S.-H. J. Org. Chem. 1986, 51, 432. (b) Corey, E. J.; Yu, C.-M.; Kim, S.-S. J. Am. Chem. Soc. 1989, 111, 5495. Roush, W. R.; Park, J. C. J. Org. Chem. 1990, 55, 1143. Hafner, A.; Duthaler, R. O.; Marti, R.; Rihs, G.; Rothe-Streit, P.; Scwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321. (e) Marshall, J. A.; Gung, W. Y. Tetrahedron 1989, 45, 1043.
10. (a) Brown, H. C.; Vara Prasad, J. V. N.; Zee, S.-H. J. Org. Chem. 1986, 51, 432. (b) Corey, E. J.; Yu, C.-M.; Kim, S.-S. J. Am. Chem. Soc. 1989, 111, 5495. Roush, W. R.; Park, J. C. J. Org. Chem. 1990, 55, 1143. Hafner, A.; Duthaler, R. O.; Marti, R.; Rihs, G.; Rothe-Streit, P.; Scwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321. (e) Marshall, J. A.; Gung, W. Y. Tetrahedron 1989, 45, 1043.
11. (a) Brown, H. C.; Vara Prasad, J. V. N.; Zee, S.-H. J. Org. Chem. 1986, 51, 432. (b) Corey, E. J.; Yu, C.-M.; Kim, S.-S. J. Am. Chem. Soc. 1989, 111, 5495. Roush, W. R.; Park, J. C. J. Org. Chem. 1990, 55, 1143. Hafner, A.; Duthaler, R. O.; Marti, R.; Rihs, G.; Rothe-Streit, P.; Scwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321. (e) Marshall, J. A.; Gung, W. Y. Tetrahedron 1989, 45, 1043.
12. (a) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (b) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827. Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. (e) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (f) Keck, G. E.; Krishnamurthy, D. Org. Synth. 1998, 62, 12.
13. (a) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (b) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827. Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. (e) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (f) Keck, G. E.; Krishnamurthy, D. Org. Synth. 1998, 62, 12.
14. (a) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (b) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827. Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. (e) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (f) Keck, G. E.; Krishnamurthy, D. Org. Synth. 1998, 62, 12.
15. (a) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (b) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827. Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. (e) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (f) Keck, G. E.; Krishnamurthy, D. Org. Synth. 1998, 62, 12.
16. (a) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (b) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827. Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. (e) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (f) Keck, G. E.; Krishnamurthy, D. Org. Synth. 1998, 62, 12.
17. (a) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (b) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827. Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. (e) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (f) Keck, G. E.; Krishnamurthy, D. Org. Synth. 1998, 62, 12.
18. The exceptions were substrate 6, which was prepared by hydrogenation of 5, and substrates 10 and 11. These materials were prepared by deprotection (DDQ) of the corresponding primary PMB ethers, followed by oxidation using the TPAP/NMO protocol of Ley. It should be noted that this approach to the preparation of β-acetoxy aldehydes for use in these reactions is complicated by the very acetate migration which makes the overall reaction possible. The only deprotection/oxidation sequences which we have been able to carry out successfully to date involve either hydrogenolysis of benzyl ethers or removal of PMB ethers using DDQ, followed by either TPAP or Dess-Martin oxidation. It is interesting to note that, although the removal of benzyl ethers using DDQ is also well established, the conditions (time and temperature) required are such that adventitious acetate migration complicates these reactions as well.
19. (5) The enolate of methyl acetate was generated by dropwise addition of methyl acetate to a stirred solution of LDA (typically 0.1 M) maintained at -78°C and used 15-30 min after addition was completed.