Stereoselective formation of α-alkylidene cyclic carbonates via carboxylative cyclization of propargyl alcohols in supercritical carbon dioxide

Journal of Organic Chemistry

Volumn 72, Issue 2, 2007, Pages 647-649

  Kayaki, Yoshihito ^a   Yamamoto, Masafumi ^a   Ikariya, Takao ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CARBON DIOXIDE; CATALYSTS;

Α-ALKYLIDENE CYCLIC CARBONATES; CARBOXYLATIVE CYCLIZATION; PROPARGYL ALCOHOLS; STEREOSELECTIVE FORMATION;

CARBONATES;

ALCOHOL DERIVATIVE; ALKYL GROUP; CARBON DIOXIDE; CARBONIC ACID DERIVATIVE; CARBOXYL GROUP; EPOXIDE; POLYMER;

ARTICLE; CARBOXYLATION; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 33846211113     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062094m     Document Type: Article

References (63)

1. Carbon Dioxide Recovery and Utilization: Aresta, M., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2003.
2. (a) Darensbourg, D. J.; Holtcamp, M. W. Coord. Chem. Rev. 1996, 153, 155-174.
3. (b) Shaikh, A. A. G.; Sivaram, S. Chem. Rev. 1996, 96, 951-976.
4. (c) Omae, I. Catal. Today 2006, 115, 33-52.
5. (a) Kihara, N.; Kara, N.; Endo, T. J. Org. Chem. 1993, 58, 6198-6202.
6. (b) Paddock, R. L.; Nguyen, S. T. J. Am. Chem. Soc. 2001, 123, 11498-11499.
7. (c) Calo, V.; Nacci, A.; Monopoli, A.; Fanizzi, A. Org. Lett. 2002, 4, 2561-2563.
8. (d) Sako, T.; Fukai, T.; Sahashi, R.; Sone, M.; Matsuo, M. Ind. Eng. Chem. Res. 2002, 41, 5353-5358.
9. (e) Shen, Y.-M.; Duan, W.-L.; Shi, M. J. Org. Chem. 2003, 68, 1559-1562.
10. (f) Huang, J.-W.; Shi, M. J. J. Org. Chem. 2003, 68, 6705-6709.
11. (g) Kawanami, H.; Sasaki, A.; Matsui, K.; Ikushima, Y. Chem. Commun. 2003, 896-897.
12. (h) Li, F.; Xia, C.; Xu, L.; Sun, W.; Chen, G. Chem. Commun. 2003, 2042-2043.
13. (i) He, L.-N.; Yasuda, H.; Sakakura, T. Green Chem. 2003, 5, 92-94.
14. (j) Paddock, R. L.; Nguyen, S. T. Chem. Commun. 2004, 1622-1623.
15. (k) Lu, X.-B.; Liang, B.; Zhang, Y.-J.; Tian, Y.-Z.; Wang, Y.-M.; Bai, C.-X.; Wang, H.; Zhang, R. J. Am. Chem. Soc. 2004, 126, 3732-3733.
16. (l) Kim, Y. J.; Varma, R. S. J. Org. Chem. 2005, 70, 7882-7891.
17. (m) Sit, W. N.; Ng, S. M.; Kwong, K. Y.; Lau, C. P. J. Org. Chem. 2005, 70, 8583-8586.
18. (n) Du, Y.; Cai, F.; Kong, D. L.; He, L. N. Green Chem. 2005, 7, 518-523.
19. (o) Mori, K.; Mitani, Y.; Hara, T.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 2005, 3331-3333.
20. (p) Du, Y.; Wang, J.-Q.; Chen, J.-Y.; Cai, F.; Tian, J.-S.; Kong, D.-L.; He, L.-N. Tetrahedron Lett. 2006, 47, 1271-1275.
21. (q) Takahashi, T.; Watahiki, T.; Kitazume, S.; Yasuda, H.; Sakakura, T. Chem. Commun. 2006, 1664-1666.
22. 2: (a) Fujinami, T.; Suzuki, T.; Kamiya, M.; Fukuzawa, S.; Sakai, S. Chem. Lett. 1985, 14, 199-200.
23. (b) Trost, B. M.; Angle, S. R. J. Am. Chem. Soc. 1985, 107, 6123-6124.
24. Dehydrative carbonylation of alcohols and analogues: (a) McGhee, W.; Riley, D. J. J. Org. Chem. 1995, 60, 6205-6207.
25. (b) Sakakura, T.; Saito, T.; Okano, M.; Choi, J.-C.; Sako, T. J. Org. Chem. 1998, 63, 7095-7096.
26. (c) Sakakura, T.; Saito, T.; Choi, J.-C.; Masuda, T.; Sako, T.; Oriyama, T. J. Org. Chem. 1999, 64, 4506-4508.
27. (d) Isaacs, N. S.; O'Sullivan, B.; Verhaelen, C. Tetrahedron 1999, 55, 11949-11956.
28. (e) Tomishige, K.; Ikeda, Y.; Sakaihoti, T.; Fujimoto, K. J. Catal. 2000, 192, 355-362.
29. (f) Choi, J.-C.; He, L.-N.; Yasuda, H.; Sakakura, T. Green Chem. 2002, 4, 230-234.
30. (g) Aresta, M.; Dibenedetto, A.; Fracchiolla, E.; Giannoccaro, P.; Pastore, C.; Pápai, I.; Schubert, G. J. Org. Chem. 2005, 70, 6177-6186.
31. 2: (a) McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205-6207.
32. (b) Salvatore, R. N.; Flanders, V. L.; Ha, D.; Jung, K. W. Org. Lett. 2000, 2, 2797-2800.
33. (c) Fujita, S.-I.; Bhanage, B. M.; Ikushima, Y.; Arai, M. Green. Chem. 2001, 3, 87-91.
34. (d) Bratt, M. O.; Taylor, P. C. J. Org. Chem. 2003, 68, 5439-5444.
35. 2: (a) Iritani, K.; Yanagihara, N.; Utimoto, K. J. Org. Chem. 1986, 51, 5499-5501.
36. (b) Inoue, Y.; Itoh, Y.; Yen, I.-F.; Imaizumi, S. J. Mol. Catal. 1990, 60, L1-L3.
37. (c) Uemura, K.; Kawaguchi, T.; Takayama, H.; Nakamura, A.; Inoue, Y. J. Mol. Catal. A: Chem. 1999, 139, 1-9.
38. d) Uemura, K.; Shiraishi, D.; Noziri, M.; Inoue, Y. Bull. Chem. Soc. Jpn. 1999, 72, 1063-1069.
39. Ru catalyst: Sasaki, Y. Tetrahedron Lett. 1986, 27, 1573-1574.
40. Co catalyst: Inoue, Y.; Ishikawa, J.; Taniguchi, M.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1987, 60, 1204-1206.
41. Cu catalysts: (a) Laas, H.; Nissen, A.; Nürrenbach, A. Synthesis 1981, 958-959.
42. (b) Kim, H.-S.; Kim, J.-W.; Kwon, S.-C.; Shim, S.-C.; Kim, T.-J. J. Organomet. Chem. 1997, 545-546, 337-344.
43. (c) Kwon, S.-C.; Cho, C.-S.; Shim, S.-C.; Kim, T.-J. Bull. Korean Chem. Soc. 1999, 20, 103-105.
44. (d) Gu, Y.; Shi, F.; Deng, Y. J. Org. Chem. 2004, 69, 391-394.
45. (a) Fournier, J.; Bruneau, C.; Dixneuf, P. H. Tetrahedron Lett. 1989, 30, 3981-3982.
46. (b) Joumier, J. M.; Fournier, J.; Bruneau, C.; Dixneuf, P. H. J. Chem. Soc., Perkin Trans. 1 1991, 3271-3274.
47. (c) Bruneau, C.; Dixneuf, P. H. J. Mol. Catal. 1992, 74, 97-107.
48. Toullec, P.; Martin, A. C.; Gio-Batta, M.; Bruneau, C.; Dixneuf, P. H. Tetrahedron Lett. 2000, 41, 5527-5531 and references therein.
49. Ochiai, B.; Endo, T. Prog. Polym. Sci. 2005, 30, 183-215.
50. Inoue, Y.; Ohuchi, K.; Yen, I. F.; Imaizumi, S. Bull. Chem. Soc. Jpn. 1989, 62, 3518-3522.
51. Kayaki, Y.; Yamamoto, M.; Suzuki, T.; Ikariya, T. Green Chem. 2006, 8, 1019-1021.
52. (a) Jessop, P. G.; Ikariya, T.; Noyori, R. Science 1995, 269, 1065-1069.
53. (b) Jessop, P. G.; Ikariya, T.; Noyori, R. Chem. Rev. 1999, 99, 475-494.
54. (c) Oakes, R. S.; Clifford, A. A.; Rayner, C. M. J. Chem. Soc., Perkin Trans. I 2001, 917-941.
55. (d) Chemical Synthesis Using Supercritical Fluids; Iessop, P. G., Leitner, W., Eds.; Wiley-VCH: Weinheim, 1999.
56. Ikariya, T.; Noyori, R. In Transition Metal Catalysed Reactions; Murahashi, S.-I., Davies, S. G., Eds.; A "Chemistry for the 21st Century" Monograph; Blackwell Science: New York, 1999; pp 1-28.
57. (a) Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183-278.
58. (b) Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224-232.
59. (c) Parrill, A. L.; Dolata, D. P. J. Mol. Struct.: THEOCHEM 1996, 370, 187-202.
60. 2 adducts have been well-studied as isolable and structurally defined compounds. (a) Margulis, T. N.; Templeton, D. H. J. Am. Chem. Soc. 1961, 83, 995-996.
61. (b) Hartzler, H. D. J. Am. Chem. Soc. 1971, 93, 4961-4962.
62. (c) Liu, Y.; Chen, X.; Xue, M.; Cao, R.; Liu, L. Synthesis 2003, 195-197.
63. Kayaki, Y.; Suzuki, T.; Noguchi, Y.; Sakurai, S.; Imanari, M.; Ikariya, T. Chem. Lett. 2002, 31, 424-425.