Organozinc reagents in DMSO solvent: Remarkable promotion of S N2′ reaction for allene synthesis

Organic Letters

Volumn 10, Issue 15, 2008, Pages 3375-3377

  Kobayashi, Koji ^a   Naka, Hiroshi ^a   Wheatley, Andrew E H ^b   Kondo, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKYNE; ALLENE; DIMETHYL SULFOXIDE; MESYLIC ACID DERIVATIVE; ORGANOMETALLIC COMPOUND; ZINC;

ARTICLE; CHEMISTRY; SYNTHESIS;

ALKADIENES; ALKYNES; DIMETHYL SULFOXIDE; MESYLATES; ORGANOMETALLIC COMPOUNDS; ZINC;

EID: 49649104515     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801249w     Document Type: Article

References (48)

1. Kcnochel, P. Jones, P. Organozinc Reagents; Oxford University Press: Oxford, 1999.
2. (a) Hoffmann-Röder, A.; Krause, N. Angew. Chem., Int. Ed. 2004, 43, 1196-1216.
3. (b) Hoffmann-Röder, A.; Krause, N. Angew. Chem., Int. Ed. 2002, 41, 2933-2935, and references therein.
4. (a) Tsukamoto, H.; Matsumoto, T.; Kondo, Y. J. Am. Chem. Soc. 2008, 130, 388-389.
5. (b) Volz, F.; Krause, N. Org. Biomol. Chem. 2007, 5, 1519-1521.
6. (c) Song, M.; Montgomery, J. Tetrahedron 2005, 61, 11440-11448.
7. (d) Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12-21.
8. (a) Kondo, Y.; Morey, J. V.; Morgan, J. C.; Naka, H.; Nobuto, D.; Raithby, P. R.; Uchiyama, M.; Wheatley, A. E. H. J. Am. Chem. Soc. 2007, 129, 12734-12738.
9. (b) Mulvey, R. E.; Mongin, F.; Uchiyama, M.; Kondo, Y. Angew. Chem., Int. Ed. 2007, 46, 3802-3824.
10. (c) Ueno, M.; Wheatley, A. E. H.; Kondo, Y. Chem. Commun. 2006, 3549-3550.
11. (d) Kobayashi, K.; Ueno, M.; Naka, H.; Kondo, Y. Chem. Commun. 2008,DOI:10.1039/B807169A.
12. (a) Rutherford, J. L.; Collum, D. B. J. Am. Chem. Soc. 2001, 123, 199-202.
13. (b) Majewski, M.; Nowak, P. Tetrahedron Lett. 1998, 39, 1661-1664.
14. (c) Winkle, M. R.; Ronald, R. C. J. Org. Chem. 1982, 47, 2101-2108.
15. (d) Shibli, A.; Varghese, J. P.; Knochel, P.; Marek, I. Synlett 2001, 818-820.
16. (a) Buncel, E.; Wilson, H. Adv. Phys. Org. Chem. 1977, 14, 133-202.
17. (b) Martin, D.; Weise, A.; Niclas, H. J. Angew. Chem., Int. Ed. Engl. 1967, 6, 318-334.
18. Some unique behaviors of the organozinc compounds in or with DMSO have been reported. (a) Okhlobystin, Y. O.; Zakharkin, I. L. J. Organomet. Chem. 1965, 257-258.
19. (b) Masao, T.; Hiroyuki, K.; Teruo, O.; Hiroshi, K. Nippon Kagaku Kaishi 1976, 356-358.
20. (c) Berk, S. C.; Yeh, M. C. P.; Jeong, N.; Knochel, P. Organometallics 1990, 9, 3053-3064.
21. (d) Grondin, J.; Sebban, M.; Vottero, P. J. Organomet. Chem. 1989, 362, 237-242.
22. (e) Hlavinka, M.; Hagadorn, J. R. Organometallics 2007, 26, 4105-4108.
23. (a) Krause, N.; Hashmi, A. S. K., Modern Allene Chemistry; Wiley-VCH, Weinheim, Germany, 2004; Vols. 1, 2.
24. (b) Krause, N.; Hoffmann-Roder, A. Tetrahedron 2004, 60, 11671-11694.
25. (c) Brummond, K. M.; DeForrest, Synthesis 2007, 795-818.
26. (d) Nakamura, H.; Kamakura, T.; Onagi, S. Org. Lett. 2006, 8, 2095-2098.
27. (e) Ogasawara, M.; Nagano, T.; Hayashi, T. J. Org. Chem. 2005, 70, 5764-5767.
28. N2′ reactions of allyl electrophiles in the presence of activators, see: (a) Arai, M.; Kawasuji, T.; Nakamura, E. Chem. Lett. 1993, 357-360.
29. (b) Kacprzynski, M. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 10676-10681.
30. (c) Merphy, K. E.; Hoveyda, A. H. Org. Lett. 2005, 7, 1255-1258.
31. (a) Katsuhira, T.; Harada, T.; Maejima, K.; Osada, A.; Oku, A. J. Org. Chem. 1993, 58, 6166-6188.
32. (b) Harada, T.; Katsuhira, T.; Osada, A.; Iwazaki, K.; Maejima, K.; Oku, A. J. Am. Chem. Soc. 1996, 118, 11377-11390.
33. (c) Varghese, J. P.; Knochel, P.; Marek, I. Org. Lett. 2000, 2, 2849-2852.
34. Reichardt, C. Angew. Chem., Int. Ed. 1979, 18, 98-100.
35. Gutmann, V.; Wychera, E. Inorg. Nucl. Chem. Lett. 1966, 257-260.
36. Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. J. Org. Chem. 1991, 56, 1445-1453.
37. Grée, D.; Grée, R. Tetrahedron Lett. 2007, 48, 5435-5438.
38. N2′ reaction, complete racemization was observed.
39. (a) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367-371.
40. (b) Corbera, J.; Font, J.; Monsalvatje, M.; Ortuno, R. M. J. Org. Chem. 1988, 53, 4393-4595.
41. (c) He, Y.-T.; Yang, H.-N.; Yao, Z.-J. Terahedron 2002, 58, 8805-8810.
42. (a) Elsevier, C. J.; Vermeer, P. J. J. Org. Chem. 1989, 54, 3726-3730.
43. (b) Marchall, J. A.; Robinson, E. D.; Zapata, A. J. Org. Chem. 1989, 54, 5854-5855.
44. (c) Myers, A. G.; Condroski, K. R. J. Am. Chem. Soc. 1995, 117, 3057-3083.
45. (d) Laux, M.; Krause, N.; Koop, U. Synlett 1996, 87-88.
46. (e) Brummond, K. M.; Kerekes, A. D.; Wan, H. J. Org. Chem. 2002, 67, 5156-5163.
47. (a) Uchiyama, M.; Koike, M.; Kameda, M.; Kondo, Y.; Sakamoto, T. T. J. Am. Chem. Soc. 1996, 118, 8793-8794.
48. (b) Ishimori, M.; Tsuruta, T. Kogyou Kagaku Zashi 1967, 70, 152-158.