Selective reduction of the carbonyl group in organomercurials. A facile method for the protection-deprotection of the mercurio group and a new route to annulated lactones

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5585-5588

  Kočovský, Pavel ^c   Dunn, Victoria ^c   Grech, Jason M ^c   Šrogl, Jiří ^a   Mitchell, William L ^b  

^a EMORY UNIVERSITY   (United States)

^b GLAXOSMITHKLINE   (United Kingdom)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0344751983     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01131-8     Document Type: Article

References (26)

1. 1. (a) Larock, R. C. Organomercury Compounds in Organic Synthesis; Springer: Berlin, 1985.
2. (b) Larock, R. C. Solvomercuration - Demercuration Reactions in Organic Synthesis, Springer: Berlin 1986.
3. (c) Kočovský, P. Organometallics 1993, 12, 1969.
4. 2. Trapping of the radical, generated by the hydride reduction, via addition to a double bond, seems to be the only notable exception: Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon: Oxford, 1986.
5. 3. (a) Collum, D. B.; Mohamadi, E; Hallock, J. H. J. Am. Chem. Soc. 1983, 105, 6882.
6. (b) Collum, D. B.; Still, W. C.; Mohamadi, F. J. Am. Chem. Soc. 1986, 108, 2094.
7. 4. Kočovský, P.; Šrogl, J.; Pour, M.; Gogoll, A. J. Am. Chem. Soc. 1994, 116, 186.
8. 5. Kočovský, P.; Grech, J. M.; Mitchell, W. L. J. Org. Chem. 1995, 60, 1482.
9. 7
10. 7. Kočovský, P.; Šrogl, J.; Gogoll, A.; Hanuš, V.; Polášek, M. J. Chem. Soc., Chem. Commun. 1992, 1086.
11. 8. (a) Dauben, W. G.; Berezin, G. H. J. Am. Chem. Soc. 1963, 85, 468.
12. (b) Kawabata, N.; Ikeda, N. Bull. Chem. Soc. Jpn. 1980, 53, 563.
13. 9. All new compounds gave satisfactory spectral and analytical data. All yields refer to isolated (preparative) yields.
14. 10. (a) Aburatani, M.; Takeuchi, T.; Mori, K. Synthesis 1987, 181.
15. (b) Wagner, A. F.; Wallis, E. S. J. Am. Chem. Soc. 1950, 72, 1047.
16. 199Hg isotope.
17. 3 gave a complementary result. (equation presented)
18. 13. Kočovský, P.; Grech, J. M.; Mitchell, W. L. Tetrahedron Lett. 1996, 37, 1125.
19. 13C NMR δ 177.3 ppm.
20. 15. Grennberg, H.; Gogoll, A.; Bäckvall, J.-E. Organometallics 1993, 12, 1790.
21. 13C NMR δ 174.3 ppm.
22. 7
23. 18. For notation, see: Kočovský, P.; Stieborová, I. J. Chem. Soc., Perkin Trans. 1 1987, 1969.
24. 19. For an overview of the methods available for construction of lactones, see, e.g.: (a) Bartlett, P. A. in "Olefin Cyclization Processes that form Carbon-Heteroatom Bonds" Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1984; Vol. 3, p. 411.
25. (b) Kočovský, P.; Tureček, F.; Hájíček, J. Synthesis of Natural Products: Problems of Stereoselectivity; CRC: Boca Raton, FL, 1986; Vol. I and II.
26. For a recent, Pd-catalyzed procedure, analogous to halolactonization, see: (c) Larock, R. C.; Hightower, T. R. J. Org. Chem. 1993, 58, 5298.