Isothiourea-catalyzed asymmetric O- to C-carboxyl transfer of furanyl carbonates

Synthesis

Volumn , Issue 12, 2011, Pages 1865-1879

  Joannesse, Caroline ^a   Morrill, Louis C ^a   Campbell, Craig D ^a   Slawin, Alexandra M Z ^a   Smith, Andrew D ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

butenolides; carboxyl transfer; furanyl carbonates; isothiourea; organocatalysis

Indexed keywords

BUTENOLIDES; CARBOXYL TRANSFER; FURANYL CARBONATES; ISOTHIOUREA; ORGANOCATALYSIS;

CATALYSIS; REACTION KINETICS; THIOUREAS;

CARBONATES;

3 (4 BROMOBENZYL) 5 (4 FLUOROPHENYL) 3 (PHENYLTHIO)DIHYDROFURAN 2 (3H)ONE; 3 (4 BROMOBENZYL) 5 PHENYL 3 (PHENYLTHIO)DIHYDROFURAN 2 (3H)ONE; 3 (4 BROMOBENZYL) 5 PHENYLFURAN 2 YL PHENYLCARBONATE; 3 ALLYL 5 (4 FLUOROPHENYL) 3 (PHENYLTHIO)DIHYDROFURAN 2 (3H)ONE; 3 ALLYL 5 PHENYL 3 (PHENYLTHIO)DIHYDROFURAN 2 (3H)ONE; 3 BENZYL 5 (4 FLUOROPHENYL) 3 (PHENYLTHIO)DIHYDROFURAN 2 (3H)ONE; 3 BENZYL 5 (4 FLUOROPHENYL)FURAN 2 YL PHENYLCARBONATE; 3 BENZYL 5 PHENYL 3 (PHENYLTHIO)DIHYDROFURAN 2 (3H)ONE; 3 BENZYL 5 PHENYLFURAN 2 YL 2,2,2 TRICHLOROETHYLCARBONATE; 3 BENZYL 5 PHENYLFURAN 2 YL PHENYLCARBONATE; 3 ETHYL 5 (4 FLUOROPHENYL) 3 (PHENYLTHIO)DIHYDROFURAN 2 (3H)ONE; 3 ETHYL 5 PHENYL 3 (PHENYLTHIO)DIHYDROFURAN 2 (3H)ONE; 3 METHYL 5 PHENYL 3 (PHENYLTHIO)DIHYDROFURAN 2 (3H)ONE; 5 (4 FLUOROPHENYL) 3 METHYL 3 (PHENYLTHIO)DIHYDROFURAN 2 (3H)ONE; 5 (4 FLUOROPHENYL) 3 METHYLFURAN 2 YL 2,2,2 TRICHLOROETHYLCARBONATE; 5 (4 FLUOROPHENYL) 3 METHYLFURAN 2 YL PHENYLCARBONATE; 5 (4 FLUROPHENYL) 3 (PHENYLTHIO)DIHYDROFURAN 2 (3H)ONE; 5 METHYL 3 PHENYLFURAN 2 (5H)ONE; 5 METHYL 3 PHENYLFURAN 2 YL PHENYLCARBONATE; 5 PHENYL 3 (PHENYLTHIO)DIHYDROFURAN 2 (3H)ONE; BUTENOLIDE; BUTYROLACTONE; CARBONIC ACID DERIVATIVE; FURANYLCARBONATE DERIVATIVE; PHENYL 2 METHYL 5 OXO 4 PHENYL 2,5 DIHYDROFURAN 2 CARBOXYLATE; PHENYL 3 METHYL 2 OXO 5 PHENYL 2,3 DIHYDROFURAN 3 CARBOXYLATE; PHENYL 5 METHYL 2 OXO 3 PHENYL 2,3 DIHYDROFURAN 3 CARBOXYLATE; PSEUDOTHIOUREA; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; SOLVENT EFFECT; STEREOISOMERISM; STRUCTURE ANALYSIS;

EID: 79958105121     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260602     Document Type: Article

References (62)

1. For representative examples, see:, Figadére B, Acc. Chem. Res. 1995 28 359
2. Tu L, Zhao Y, Yu Z, Cong Y, Xu G, Peng L, Zhang P, Cheng X, Zhao Q, Helv. Chim. Acta 2008 91 1578
3. deGuzman F S., Schmitz F J., J. Nat. Prod. 1990 53 926
4. Evidente A, Sparapano L, J. Nat. Prod. 1994 57 1720
5. Dogné J, Supuran C T., Pratico D, J. Med. Chem. 2005 48 2251
6. Braña M F., García M L., Lpez B, dePascual-Teresa B, Ramos A, Pozuelo J M., Domínguez M T., Org. Biomol. Chem. 2004 2 1864
7. Singh R P., Foxman B M., Deng L, J. Am. Chem. Soc. 2010 132 9558
8. Brown S P., Goodwin N C., MacMillan D W. C., J. Am. Chem. Soc. 2003 125 1192
9. Shaw S A., Aleman P, Christy J, Kampf J W., Va P, Vedejs E, J. Am. Chem. Soc. 2006 128 925-934
10. For an excellent recent review of Lewis base mediated reaction processes, see:, Denmark S E., Beutner G L., Angew. Chem. Int. Ed. 2008 47 1560
11. For examples of our previous research programme concerned with applications of NHCs in organocatalysis, see:, Thomson J E., Rix K, Smith A D., Org. Lett. 2006 8 3785
12. Thomson J E., Campbell C D., Concellón C, Duguet N, Rix K, Slawin A M. Z., Smith A D., J. Org. Chem. 2008 73 2784
13. Campbell C D., Duguet N, Gallagher K A., Thomson J E., Lindsay A G., ODonoghue A, Smith A D., Chem. Commun. 2008 3528
14. Duguet N, Campbell C D., Slawin A M. Z., Smith A D., Org. Biomol. Chem. 2008 6 1108
15. Thomson J E., Kyle A F., Concellón C, Gallagher K A., Lenden P, Morrill L C., Miller A J., Joannesse C, Slawin A M. Z., Smith A D., Synthesis 2008 2805
16. Concellón C, Duguet N, Smith A D., Adv. Synth. Catal. 2009 351 3001
17. Duguet N, Donaldson A, Leckie S M., Douglas J, Shapland P, Churchill G, Slawin A M. Z., Smith A D., Tetrahedron: Asymmetry 2010 21 582
18. Duguet N, Donaldson A, Leckie S M., Shapland P, Slawin A M. Z., Smith A D., Tetrahedron: Asymmetry 2010 21 601
19. Douglas J, Ling K B., Concellón C, Churchill G, Slawin A M. Z., Smith A D., Eur. J. Org. Chem. 2010 5863
20. Ling K B., Smith A D., Chem. Commun. 2011 47 373
21. Campbell C D., Collett C J., Thomson J E., Slawin A M. Z., Smith A D., Org. Biomol. Chem. 2011 9 4205
22. For examples of our previous research programme concerned with applications of isothioureas in organocatalysis, see:, Joannesse C, Simal C, Concellón C, Thomson J E., Campbell C D., Slawin A M. Z., Smith A D., Org. Biomol. Chem. 2008 6 2900
23. Woods P A., Morrill L C., Lebl T, Slawin A M. Z., Bragg R A., Smith A D., Org. Lett. 2010 12 2660
24. Belmessieri D, Joannesse C, Woods P A., MacGregor C, Jones C, Campbell C D., Johnston C P., Duguet N, Concellón C, Bragg R A., Smith A D., Org. Biomol. Chem. 2011 9 559
25. Belmessieri B, Morrill L C., Simal C, Slawin A M. Z., Smith A D., J. Am. Chem. Soc. 2011 133 2714
26. For initial work, see
27. Steglich W, Höfle G, Tetrahedron Lett. 1970 11 4727
28. Ruble J C., Fu G C., J. Am. Chem. Soc. 1998 120 11532
29. Shaw S A., Aleman P, Vedejs E, J. Am. Chem. Soc. 2003 125 13368
30. Nguyen H V., Butler D C. D., Richards C J., Org. Lett. 2006 8 769
31. Busto E, Gotor-Fernández V, Gotor V, Adv. Synth. Catal. 2006 348 2626
32. Seitzberg J G., Dissing C, Stofte I, Norrby P.-O, Johannsen M, J. Org. Chem. 2005 70 8332
33. Dietz F R., Gröger H, Synlett 2008 663
34. Dietz F R., Gröger H, Synthesis 2009 4208
35. Uraguchi D, Koshimoto K, Miyake S, Ooi T, Angew. Chem. Int. Ed. 2010 49 5567
36. Zhang Z, Xie F, Jia J, Zhang W, J. Am. Chem. Soc. 2010 132 15939
37. Joannesse C, Johnston C P., Concellón C, Simal C, Philp D, Smith A D., Angew. Chem. Int. Ed. 2009 48 8914
38. Selected alternative applications of chiral isothioureas in asymmetric catalysis are listed herein. For kinetic resolutions using anhydrides as acylating agents, see
39. Birman V B., Jiang H, Li X, Geo V, Uffman E W., J. Am. Chem. Soc. 2006 128 6536
40. Birman V B., Li X, Org. Lett. 2006 8 1351
41. Birman V B., Geo L, Org. Lett. 2006 8 4859
42. Birman V B., Jiang H, Li X, Org. Lett. 2007 9 3237
43. Birman V B., Li X, Org. Lett. 2008 10 1115
44. Yang X, Birman V B., Adv. Synth. Catal. 2009 351 2525
45. Xu Q, Zhou H, Geng X, Chen P, Tetrahedron 2009 65 2232
46. Belmessieri D, Joannesse C, Woods P A., MacGregor C, Jones C, Campbell C D., Johnston C P., Duguet N, Concellón C, Bragg R A., Smith A D., Org. Biomol. Chem. 2011 9 559
47. Shiina I, Nakata K, Tetrahedron Lett. 2007 48 8314
48. Shiina I, Nakata K, Sugimoto M, Onda Y, Iizumi T, Ono K, Heterocycles 2009 77 801
49. Yang X, Birman V B., Adv. Synth. Catal. 2009 351 2301
50. Shiina I, Nakata K, Heterocycles 2010 80 169
51. Shiina I, Nakata K, Onda Y, Eur. J. Org. Chem. 2008 5887
52. Shiina I, Nakata K, Ono K, Sugimoto M, Sekiguchi A, Chem. Eur. J. 2010 16 167
53. Nakata K, Onda Y, Ono K, Shiina I, Tetrahedron Lett. 2010 51 5666
54. Shiina I, Ono K, Nakata K, Chem. Lett. 2011 40 147
55. The selenation/elimination sequence was based upon literature precedent in these systems:, Pour M, Spulák M, Balsánek V, Kunes J, Kubanová P, Buchta V, Bioorg. Med. Chem. 2003 11 2843
56. White J D., Somers T C., Reddy G N., J. Org. Chem. 1992 57 4991
57. Donohoe T J., Harris R M., Burrows J, Parker J, J. Am. Chem. Soc. 2006 128 13704
58. 2O at -20 C gave <10% conversion to C -carboxy products, that was assumed to be due to low solubility of 1 at these temperatures
59. For representative examples that demonstrate the preference of substituents adjacent to an N -acyl group in heterocyclic compounds to adopt a pseudoaxial position, see:, Sinclair P J., Zhai D, Reibenspies J, Williams R M. J., J. Am. Chem. Soc. 1986 108 1103
60. Dellaria J F., Santarsiero B D., J. Org. Chem. 1989 54 3916
61. Drew M G. B., Harwood L M., Park G, Price D W., Tyler S N. G., Park C R., Cho S G., Tetrahedron 2001 57 5641
62. Anderson R J., Adams K G., Chinn H R., Henrick C A., J. Org. Chem. 1980 45 2229