Regioselective reductive opening of substituted phthalans: synthetic applications

Tetrahedron

Volumn 64, Issue 19, 2008, Pages 4275-4286

  García, Daniel ^a   Foubelo, Francisco ^a   Yus, Miguel ^a  

^a Departamento de Química Orgánica   (Spain)

Author keywords

DTBB catalysed lithiation; Reductive ring opening; SE reaction; Substituted phthalans

Indexed keywords

1 ([2 (HYDROXYMETHYL)NAPHTHALEN 1 YL]METHYL) CYCLOHEXANOL; 1 ([3 (HYDROXYMEHTYL)BIPHENYL 2 YL]METHYL) CYCLOHEXANOL; 1 [2 (HYDROXYMETHYL)NAPHTHALEN 1 YL] 2 METHYL PROPAN 2 OL; 1 [2 (HYDROXYMETHYL)NAPHTHALEN 1 YL] 3,3 DIMETHYL BUTAN 2 OL; 1 [3 (HYDROXYMETHYL)BIPHENYL 2 YL] 3,3 DIMETHYL BUTAN 2 OL; 1 HYDROXYMETHYL 2 METHYLNAPTHALENE; 1,3 DIHYDRONAPHTHOL[2,1 C]FURAN; 2 [2 (HYDROXYMETHYL)NAPHTHALEN 1 YL] 1 PHENYL ETHANOL; 2 [3 (HYDROXYMETHYL)BIPHENYL 2 YL] 1 PHENYL ETHANOL; 2 HYDROXYMETHYL 1 METHYLNAPHTHALENE; 2 HYDROXYMETHYL 3 METHYLANISOLE; 2 PHENYL 2,4 DIHYDROBENZO[F]ISOCHROMAN; 2,2 DIETHYL 2,4 DIHYDROBENZO[F]ISOCHROMAN; 2,5 DIHYRPFUROL[3,4 F]PHTHALAN; 3 ([2 (HYDROXYMETHYL)NAPHTJALEN 1 YL]METHYL) PENTAN 3 OL; 3 HYDROXYMETHYL 4 METHYLBIPHENYL; 3,3 DIETHYL 6 METHOXYISOCHROMAN; 4 HYDROXYMETHYL 3 METHYLANISOLE; 4 METHOXYPHTHALAN DERIVATIVE; 4 PHENYLPHTHALAN; 5 HYDROXYMETHYL 6 METHYLPHTHALAN; 5 METHOXYPHTHALAN DERIVATIE; 5 METHOZYPHTHALAN; 5 PHENYLPHTHALAN; 6 ([2 (HYROXYMETHYL)NAPHTHALEN 1 YL]METHYL) UNDECAN 6 OL; ANION; BENZILIC ACID; CARBONYL DERIVATIVE; ORGANOLITHIUM COMPOUND; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; LITHIATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 41549162312     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.02.072     Document Type: Article

References (62)

1. For reviews, see:. Nájera C., and Yus M. Trends Org. Chem. 2 (1991) 155-181
2. Nájera C., and Yus M. Org. Prep. Proced. Int. 27 (1995) 383-456
3. Nájera C., and Yus M. Recent Res. Dev. Org. Chem. 1 (1997) 67-96
4. Nájera C., and Yus M. Curr. Org. Chem. 7 (2003) 867-926
5. Nájera C., Sansano J.M., and Yus M. Tetrahedron 59 (2003) 9255-9302
6. Chinchilla R., Nájera C., and Yus M. Chem. Rev. 104 (2004) 2667-2722
7. Chinchilla R., Nájera C., and Yus M. Tetrahedron 61 (2005) 3139-3176
8. Yus M., and Foubelo F. In: Knochel P. (Ed). Functionalized Organometallics Vol. 1 (2005), Wiley-VCH, Weinheim Chapter 2
9. Nájera C., and Yus M. In: Rappoport Z., and Marek I. (Eds). The Chemistry of Organolithium Compounds Vol. 2 (2006), J. Wiley & Sons, Chichester, UK Chapter 3
10. Chinchilla R., Nájera C., and Yus M. ARKIVOC x (2007) 152-231
11. For monographs, see:
12. Wakefield B.J. Organolithium Methods (1988), Academic, London
13. In: Sapse A.M., and von Ragué Schleyer P. (Eds). Lithium Chemistry: A Theoretical and Experimental Overview (1995), J. Wiley & Sons, New York, NY
14. Gray M., Tinkel M., and Snieckus V. In: Abel E.W., Stone F.G.A., Wilkinson G., and McKillop A. (Eds). Comprehensive Organometallic Chemistry II Vol. 11 (1995), Pergamon, Oxford 1-92
15. Clayden J. Organolithiums: Selectivity for Synthesis (2002), Pergamon, Oxford For a review on metal-promoted dehalogenation, see:
16. Alonso F., Beletskaya I.P., and Yus M. Chem. Rev. 102 (2002) 4009-4091
17. For a recent issue of Tetrahedron Symposium-in-Print devoted to 'Functionalised Organolithium Compounds' (Guest Eds.: Nájera, C.; Yus, M.), see:. Tetrahedron 61 (2005) 3125-3450
18. For reviews, see:
19. Yus M., and Foubelo F. Rev. Heteroatom Chem. 17 (1997) 73-107
20. Yus M., and Foubelo F. In: Attanasi O.A., and Spinelli D. (Eds). Targets in Heterocyclic Systems (2002), Italian Society of Chemistry, Rome 136-171
21. Yus M. Pure Appl. Chem. 75 (2003) 1453-1475
22. Yus M., and Foubelo F. Adv. Heterocycl. Chem. 91 (2006) 135-158
23. For reviews on the arene-catalysed lithiation, see:
24. Yus M. Chem. Soc. Rev. 25 (1996) 155-161
25. Ramón D.J., and Yus M. Eur. J. Org. Chem. (2000) 225-237
26. Yus M. Synlett (2001) 1197-1205
27. Yus M. In: Rappoport Z., and Marek I. (Eds). The Chemistry of Organolithium Compounds Vol. 1 (2004), J. Wiley & Sons, Chichester, UK Part 1, Chapter 11. For a polymer supported arene-catalysed version of this reaction, see:
28. Gómez C., Ruiz S., and Yus M. Tetrahedron Lett. 39 (1998) 1397-1400
29. Gómez C., Ruiz S., and Yus M. Tetrahedron 55 (1999) 7017-7026
30. Yus M., Candela P., and Gómez C. Tetrahedron 58 (2002) 6207-6210
31. Alonso F., Candela P., Gómez C., and Yus M. Adv. Synth. Catal. 345 (2003) 275-279
32. Candela P., Gómez C., and Yus M. Russ. J. Org. Chem. 40 (2004) 795-801
33. Almena J., Foubelo F., and Yus M. Tetrahedron 51 (1995) 3351-3364
34. Azzena U., Demartis S., and Melloni G. J. Org. Chem. 61 (1996) 4913-4919
35. For a preliminary communication, see:. Foubelo F., García D., Moreno B., and Yus M. Tetrahedron Lett. 48 (2007) 3379-3383
36. Bestmann H.J., and Both W. Chem. Ber. 107 (1974) 2926-2930
37. See also:. Amijs C.H.M., van Klink G.P.M., and van Koten G. Green Chem. 5 (2003) 470-474
38. Kirmse W., and Kund K. J. Org. Chem. 55 (1990) 2325-2332
39. We have recently demonstrated that in the arene-catalysed lithiation a dianion is the intermediate for the electron transfer to the substrate:
40. Yus M., Herrera R.P., and Guijarro A. Tetrahedron Lett. 42 (2001) 3455-3458
41. Yus M., Herrera R.P., and Guijarro A. Chem.-Eur. J. 8 (2002) 2574-2584
42. Yus M., Herrera R.P., and Guijarro A. Tetrahedron Lett. 44 (2003) 1309-1312
43. Herrera R.P., Guijarro A., and Yus M. Tetrahedron Lett. 44 (2003) 1313-1316
44. Yus M., Herrera R.P., and Guijarro A. Tetrahedron Lett. 47 (2006) 6267-6271
45. Melero C., Pérez H., Guijarro A., and Yus M. Tetrahedron Lett. 48 (2007) 4105-4109
46. Melero C., Guijarro A., Baumann V., Pérez-Jiménez A.J., and Yus M. Eur. J. Org. Chem. (2007) 5514-5526
47. Melero C., Herrera R.P., Guijarro A., and Yus M. Chem.-Eur. J. 13 (2007) 10096-10107
48. In a recent paper on the reductive cleavage of an alkyl naphthyl thioether, Donohoe, Compton and co-workers proved that at 20 °C the dissociation of alkyl carbon-sulfur bond occurs after the substrate accepts a single electron (radical-anion), however, at -78 °C the radical-anion is stabilised at sufficiently longer timescales to accept a second electron, leading to the corresponding dianion, which cleaves at the aryl-sulfur bond:. Paddon C.A., Bhatti F.L., Donohoe T.J., and Compton R.G. Chem. Commun. (2006) 3402-3404
49. Witalski B., and Stengel T. Angew. Chem., Int. Ed. 38 (1999) 2426-2430
50. 2=H) was prepared from 3-phenylprop-2-yn-1-ol by propargylation with propargyl bromide (NaH, DMF, rt) following the general reported procedure. See, for instance:. Martín-Matute B., Nevado C., Cárdenas D.J., and Echavarren A. J. Am. Chem. Soc. 125 (2003) 5757-5766
51. The proton abstraction can occur at the α-position of THF. See, for instance:. Clayden J., and Yasin S.A. New J. Chem. 26 (2002) 191-192
52. The other possible regioisomeric intermediates (15′, 16′) would afford the corresponding final regioisomers of compounds 17 and 18:{A figure is presented}
53. Hashmi A.S.K., Weyrauch J.P., Kurpejovic E., Frost T.M., Miehlich B., Frey W., and Bats J.W. Chem.-Eur. J. 12 (2006) 5806-5814
54. 14,17 and shown in Scheme 6 is as follows:{A figure is presented}
55. Yus M., Moreno B., and Foubelo F. Synthesis (2004) 1115-1118
56. Zippi E.M. Synth. Commun. 24 (1994) 2515-2523
57. Seigal B.A., An M.H., and Snapper M.L. Angew. Chem., Int. Ed. 44 (2005) 4929-4932
58. Grigg R., and Stevenson R.S.P. J. Chem. Soc., Perkin Trans. 1 (1988) 1357-1364
59. Plummer E.L., Cardis A.B., Martinez A.J., VanSaun W.A., Palmere R.M., Pincus D.S., and Stewart R.B. Pestic. Sci. 14 (1983) 560-570
60. Carter S.D., and Wallace T.W. Synthesis (1983) 1000-1002
61. Ranchella M., Rol C., and Sebastiani G.V. J. Chem. Soc., Perkin Trans. 2 (2000) 311-315
62. Moorthy J.N., Venkatakrishnan P., Mal P., and Venugopalan P. J. Org. Chem. 68 (2003) 327-330