Synthesis of [2H,13C]-labelled diallylmalonates - Useful probes for the study of transition metal-catalysed 1,6-diene cycloisomerisation

European Journal of Organic Chemistry

Volumn , Issue 9, 2001, Pages 1635-1642

  Bray, Katharine L ^a   Lloyd Jones, Guy C ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

Allylmalonates; Cycloisomerisation; Isotopic labelling

Indexed keywords

ALKADIENE; ANION; BENZOIC ACID; CARBON 13; DICARBOXYLIC ACID; HYDROGEN; LEAD; MALONIC ACID; METAL;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; ISOMERISM; ISOTOPE LABELING; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0035039849     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200105)2001:9<1635::aid-ejoc1635>3.0.co;2-c     Document Type: Article

References (47)

1. Reviews: [1a] B. M. Trost, Acc. Chem. Res. 1990, 23, 34-42.
2. [1b] B. M. Trost, M. J. Krische, Synlett 1998, 1-15.
3. A. Bright, J. F. Malone, J. K. Nicholson, J. Powell, B. L. Shaw, J. Chem. Soc., Chem. Commun. 1971, 712-713.
4. [3a] R. Grigg, T. R. B. Mitchell, A. Ramasubbu, J. Chem. Soc., Chem. Commun. 1979, 669-670.
5. [3b] R. Grigg, T. R. B. Mitchell, A. Ramasubbu, J. Chem. Soc., Chem. Commun. 1980, 27-28.
6. [3c] R. Grigg, J. F. Malone, T. R. B. Mitchell, A. Ramasubbu, R. M. Scott, J. Chem. Soc., Perkin Trans. 1 1984, 1745-1754.
7. E. Schmitz, R. Urban, G. Zimmermann, J. Prakt. Chem. 1976, 318, 185;
8. E. Schmitz, U. Hench, D. Habisch, J. Prakt. Chem. 1976, 318, 471.
9. Y. Yamamoto, N. Ohkoshi, M. Kameda, K. Itoh, J. Org. Chem. 1999, 64, 2178-2179.
10. B. Radetich, T. V. RajanBabu, J. Am. Chem., Soc. 1998, 120, 8007-8008.
11. A. Heumann, M. Moukhliss, Synlett 1998, 1211-1212.
12. Note that cycloisomerisation is not always a desirable reaction - for example, it recently was reported to be a seriously competing side reaction (43%) in a Ru-catalysed ring-closing metathesis of N-tosyl diallyl amine. See: A. Fürstner, M. Liebl, C. W. Lehmann, M. Picquet, R. Kunz, C. Bruneau, D. Touchard, P. H. Dixneuf, Chem. Eur. J. 2000, 6, 1847-1857.
13. [9a] W. E. Piers, P. J. Shapiro, E. E. Bunel, J. E. Bercaw, Synlett 1990, 74-84.
14. [9b] K. S. Knight, R. M. Waymouth, J. Am. Chem. Soc. 1991, 113, 6268-6270.
15. [9c] G. A. Molander, J. O. Hoberg, J. Am. Chem. Soc. 1992, 114, 3123-3126.
16. [9d] E.-I. Negishi, T. Takahashi, Acc. Chem. Res. 1994, 27, 124-130.
17. [9e] U. M. Dzhemilev, Tetrahedron 1995, 51, 4333-4346.
18. [9f] J. Christoffers, R. G. Bergman, J. Am. Chem. Soc. 1996, 118, 4715-4716.
19. [9g] S. Thiele, G. Erker, Chem. Ber./Recueil 1997, 130, 201-207.
20. [10a] P. Denn, L. Fensterbank, M. Malacria, Tetrahedron Lett. 1998, 39, 833-836.
21. [10b] D. Stein, R. Samy, R. Nouguier, D. Crich, M. P. Bertrand, J. Org. Chem. 1997, 62, 275-286.
22. [10c] A. M. Bernard, P. P. Piras, P. Toriggia, Synthesis 1990, 527-529.
23. G. C. Lloyd-Jones, Synlett 2001, 161-183.
24. K. L. Bray, G. C. Lloyd-Jones, unpublished results
25. 1]propen-1-yl carbonate: [13a] Y. Xu, B. Zhou, J. Org. Chem. 1987, 52, 974-977.
26. 6]-1,3-dibromopropane with diethyl malonate: [13b] J. A. van Zee, A. L. Kwiram, J. Am. Chem. Soc. 1990, 112, 5012-5018.
27. J. Schwartz, J. A. Labinger, Angew. Chem., Int. Ed. Engl. 1976, 15, 333-339.
28. S. L. Buchwald, S. J. Lamaire, R. B. Nielsen, B. T. Watson, Organic Synth. 1992, 71, 77-82.
29. 2 (see reference [17c]) effected very clean deprotection and gave aldehyde 16 in 74% yield.
30. [17a] F. Huet, A. Levchevallier, M. Pellet, J. M. Conia, Synthesis 1978, 63-65.
31. [17b] M. Mikolajczyk, P. Balczewski, Synthesis 1987, 659-661.
32. [17c] R. A. Ellison, E. R. Lukenbach, C.-W. Chiu, Tetrahedron Lett. 1975, 499-502.
33. 3, NaH, 0°C or KOtBu, -78°C to room temp.
34. 3][I] and BuLi gave no trace (< 1%) of the desired alkene 2. Even though the red colour of the ylide was fully discharged after 24 h at reflux.
35. P. J. H. Carlsen, T. Katsuki, V. S. Martin, B. Sharpless, J. Org. Chem. 1981, 46, 3936-3938.
36. J. Tsuji, Palladium Reagents and Catalysts, Innovations in Organic Synthesis, Wiley, Chichester, UK, 1995.
37. 1]Prop-2-en-1-ol: H. Badawi, P. Lorencak, K. W. Hillig, M. Imachi, R. L. Kuczkowski, J. Mol. Struct. 1987, 162, 247-254.
38. 1]-1-Chloroprop-2-ene: W. Kirmse, V. Zellmer, B. Goer, J. Am. Chem. Soc. 1986, 108, 4912-4917.
39. 1]-1-Bromoprop-2-ene: G. A. Olah, C. L. Jeuell, A. M. White, J. Am. Chem. Soc. 1969, 91, 3961-3962.
40. 31P NMR) were obtained and we suspect that irreversible deprotonation of 20 leads to decomposition of the enolate to give volatile products arising by fragmentation.
41. 1H becomes redistributed by exchange of protons between the resulting the phosphonium salt and the ylide. See: H. J. Bestmann, Chem. Ber. 1962, 95, 58-63.
42. M. Hesse, H. Meier, B. Zech, Spectroscopic Methods in Organic Chemistry, Stuttgart, Germany, 1997.
43. K. L. Bray, I. J. S. Fairlamb, G. C. Lloyd-Jones, Chem. Commun. 2001, 187-188.
44. K. L. Bray, I. J. S. Fairlamb, P. J. Kaiser, G. C. Lloyd-Jones, P. A. Slatford, unpublished results.
45. [28a] J. Krause, G. Cestaric, K.-J. Haack, K. Seevogel, W. Storm, K.-R. Pörschke, J. Am. Chem. Soc. 1999, 121, 9807-9823.
46. [28b] M. Gómez Andreu, A. Zapf, M. Beller, Chem. Commun. 2000, in press.
47. S. Hashiguchi, Y. Maeda, S. Kishimoto, M. Ochiai, Heterocycles 1986, 24, 2273-2283.