Synthesis of α-hydroxyallenes by copper-catalyzed S N2′substitution of propargylic dioxolanones

European Journal of Organic Chemistry

Volumn , Issue 17, 2009, Pages 2836-2844

  Tang, Xiaoping ^a   Woodward, Simon ^a   Krause, Norbert ^b  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b TU DORTMUND UNIVERSITY   (Germany)

Author keywords

Allenes; Copper; Grignard reaction; Homogeneous catalysis; Nucleophilic substitution

Indexed keywords

EID: 66449127403     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900226     Document Type: Article

References (53)

1. a) N Krause, A. S. K. Hashmi (Eds.), Modern Allenes Chemistry, Wiley-VCH: Weinheim, 2004;
2. b) A. Hoffmann-Röder, N. Krause, Angew. Chem. Int. Ed. 2002, 41, 2933-2935;
3. c) N. Krause, A. Hoffmann-Röder, J. Canisius, Synthesis 2002, 1759-1774;
4. d) J. A. Marshall, J. Org. Chem. 2007, 72, 8153-8166.
5. For reviews see: a) D. J. Pasto, Tetrahedron 1984, 40, 205-2827;
6. b) K. M. Brummond, J. E. DeForrest, Synthesis 2007, 6, 795818;
7. c) N. Krause, A. Hoffmann-Röder, Tetrahedron 2004, 60, 11671-11694.
8. R. W. Herr, D. M. Wieland, C. R. Johnson, J. Am. Chem. Soc. 1970, 92, 3813-3814.
9. A. Alexakis, I. Marek, P. Mangeney, J. F. Normant, J. Am. Chem. Soc. 1990, 112, 8042-8047.
10. M. Mae, J. A. Hong, B. Xu, G. B. Hammond, Org. Lett. 2006, 8, 479-482.
11. P. Rona, P. Crabbe, J. Am. Chem. Soc. 1968, 90, 4733-4734.
12. A. Alexakis, P. Mangeney, J. F. Normant, Tetrahedron Lett. 1985, 26, 4197-4200.
13. H. Westmuze, P. Vermeer, Synthesis 1979, 390-392.
14. For other selected example see: a) R. S. Macomber, J. Am. Chem. Soc. 1977, 99, 3072-3075;
15. b) A. G. Myers, B. Zheng, J. Am. Chem. Soc. 1996, 118, 4492-4493;
16. c) R. B. Chedid, M. Brummer, B. Wibbeling, R. Fröhlich, D. Hoppe, Angew. Chem. Int. Ed. 2007, 46, 3131-3134.
17. a) T. L. Macdonald, D. R. Reagan, J. Org. Chem. 1980, 45, 4740-4747;
18. b) C. Deutsch, B. H. Lipshutz, N. Krause, Angew. Chem. Int. Ed. 2007, 46, 1650-1653.
19. a) A. Alexakis, I. Marek, P. Mangeney, J. F. Normant, J. Am. Chem. Soc. 1990, 112, 8042-8047;
20. b) M. H. Nantz, D. M. Bender, S. Janaki, Synthesis 1993, 577-578.
21. F. Bertozzi, P. Crotti, F. Macchia, M. Pineschi, A. Arnold, B. L. Feringa, Tetrahedron Lett. 1999, 40, 4893-4896.
22. H. Ito, Y. Sasaki, M. Sawamura, J. Am. Chem. Soc. 2008, 130, 15774.....15775.
23. a) P.R. Ortiz De Montellano, J. Chem. Soc., Chem. Commun. 1973, 709-710;
24. b) A. Alexakis, I. Marek, P. Mangeney, J. F. Normant, Tetrahedron 1991, 47, 1677-1696;
25. c) C. Deutsch, A. Hoffmann-Röder, A. Domke, N. Krause, Synlett 2007, 5, 737740.
26. a) G. Zweifel, S. J. Backlund, T. Leung, J. Am. Chem. Soc. 1978, 700, 5561-5562;
27. b) E. Hernandez, J. A. Soderquist, Org. Lett. 2005, 7, 5397-5400;
28. c) D. J. Rodini, B. B. Snider, Tetrahedron Lett. 1980, 21, 3857-3860.
29. a) A. Horvath, J.-E. Backvall, J. Org. Chem. 2001, 66, 81208126;
30. b) M. Bertrand, G. Gil, J. Viala, Tetrahedron Lett. 1979, 20, 1595-1598;
31. c) M. Yoshida, T. Gotou, M. Ihara, Chem. Commun. 2004, 1124-1125.
32. a) A. Hoffmann-Röder, N. Krause, Org. Lett. 2001, 3, 25372538;
33. b) A. Hoffmann-Röder, N. Krause, Org. Biomol. Chem. 2005, 3, 387-391;
34. c) C.-Y. Zhou, P.W.H. Chan, C.-M. Che, Org. Lett. 2006, 8, 325-328;
35. d) A. S. K. Hashmi, L. Schwarz, J. H. Choi, T. M. Frost, Angew. Chem. Int. Ed. 2000, 39, 22852288;
36. e) L.-P. Liu, B. Xu, M. S. Mashuta, G. B. Hammond, J. Am. Chem. Soc. 2008, 130, 17642-17643.
37. For review on asymmetric dihydroxylation see: H.C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547.
38. 2O, detail see experimental section. Also see: G. J. Kubas, Inorg. Synth. 1990, 28, 68.
39. For review see: a) E.-I. Negishi, L. Anastasia, Chem. Rev. 2003, 103, 1979-2017;
40. b) H. Doucet, J.-C. Hierso, Angew. Chem. Int. Ed. 2007, 46, 834-871.
41. a) K.-S. Jeong, P. Sjo, K. B. Sharpless, Tetrahedron Lett. 1992, 33, 3833-3836;
42. b) K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu, X.-L. Zhang, J. Org. Chem. 1992, 57, 2768-2771.
43. B. Plietker, M. Niggemann, Org. Lett. 2003, 5, 3353-3356.
44. A. Alexakis, C. Benhaim, S. Rosset, M. Humam, J. Am. Chem. Soc. 2002, 124, 5262-5263.
45. a) A. Boudier, L. A. Bromm, M. Lotz, P. Knochel, Angew. Chem. Int. Ed. 2000, 39, 4414-4435;
46. b) C. Deutsch, A. Hoffmann-Roder, A. Domke, N. Krause, Synlett 2007, 07370740.
47. A. Alexakis, Pure Appl. Chem. 1992, 64, 387-392.
48. J. Waser, J. C. Gonzalez-Gomez, H. Nambu, P. Huber, E. M. Carreira, Org. Lett. 2005, 19, 4249-4252.
49. R. D. Singer, A. C. Oehlschlager, J. Org. Chem. 1992, 57, 21922195.
50. W. D. Inman, K. A. J. Sanchez, M. A. Chaidez, D. R. Paulson, J. Org. Chem. 1989, 54, 4872-4881.
51. D. W. Knight, D. E. Shaw, E. R. Staples, Eur. J. Org. Chem. 2004, 9, 1973-1982.
52. M. J. Brown, T. Harrison, L. E. Overman, J. Am. Chem. Soc. 1991, 113, 5378-5384.
53. A. Alexakis, I. Marek, P. Mangeney, J. F. Normant, Tetrahedron 1991, 47, 1677-1696.