Tetrasubstituted allene ethers; synthesis and use in Nazarov reactions

Synthesis

Volumn , Issue 5, 2004, Pages 786-790

  Tokeshi, Bradley K ^a   Tius, Marcus A ^a  

^a UNIVERSITY OF HAWAII   (United States)

Author keywords

Alkynes; Allenes; Cyclizations; Ethers; Nazarov reactions; Rearrangements

Indexed keywords

ETHERS; ORGANIC COMPOUNDS; ORGANIC SOLVENTS; REACTION KINETICS; SUBSTITUTION REACTIONS;

ALLENE ETHERS; NAZAROV CYCLIZATION REACTION; NAZAROV REACTIONS;

SYNTHESIS (CHEMICAL);

ALLENE DERIVATIVE; ESTER DERIVATIVE;

ARTICLE; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 1942521129     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-815994     Document Type: Article

References (40)

1. Hu, H.; Smith, D.; Cramer, R. E.; Tius, M. A. J. Am. Chem. Soc. 1999, 121, 9895.
2. For some approaches to the synthesis of allenes, see: (a) Huang, X.; Xiong, Z.-C. Chem. Commun. 2003, 1714. (b) Huang, X.; Xiong, Z.-C. Tetrahedron Lett. 2003, 44, 5913. (c) Fukuhara, K.; Okamoto, S.; Sato, F. Org. Lett. 2003, 5, 2145. (d) Ma, S.; Hou, H.; Zhao, S.; Wang, G. Synthesis 2002, 1643. (e) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (f) Inoue, H.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. Tetrahedron 2002, 58, 83. (g) Satoh, T.; Sakamoto, T.; Watanabe, M. Tetrahedron Lett. 2002, 43, 2043. (h) Prabharasuth, R.; Van Vranken, D. L. J. Org. Chem. 2001, 66, 5256. (i) Hamada, T.; Mizojiri, R.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2000, 722, 7138. (j) Tius, M. A.; Pal, S. K. Tetrahedron Lett. 2001, 42, 2605. (k) Silveira, C. C.; Boeck, P.; Braga, A. L. Tetrahedron Lett. 2000, 41, 1867.
3. For some approaches to the synthesis of allenes, see: (a) Huang, X.; Xiong, Z.-C. Chem. Commun. 2003, 1714. (b) Huang, X.; Xiong, Z.-C. Tetrahedron Lett. 2003, 44, 5913. (c) Fukuhara, K.; Okamoto, S.; Sato, F. Org. Lett. 2003, 5, 2145. (d) Ma, S.; Hou, H.; Zhao, S.; Wang, G. Synthesis 2002, 1643. (e) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (f) Inoue, H.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. Tetrahedron 2002, 58, 83. (g) Satoh, T.; Sakamoto, T.; Watanabe, M. Tetrahedron Lett. 2002, 43, 2043. (h) Prabharasuth, R.; Van Vranken, D. L. J. Org. Chem. 2001, 66, 5256. (i) Hamada, T.; Mizojiri, R.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2000, 722, 7138. (j) Tius, M. A.; Pal, S. K. Tetrahedron Lett. 2001, 42, 2605. (k) Silveira, C. C.; Boeck, P.; Braga, A. L. Tetrahedron Lett. 2000, 41, 1867.
4. For some approaches to the synthesis of allenes, see: (a) Huang, X.; Xiong, Z.-C. Chem. Commun. 2003, 1714. (b) Huang, X.; Xiong, Z.-C. Tetrahedron Lett. 2003, 44, 5913. (c) Fukuhara, K.; Okamoto, S.; Sato, F. Org. Lett. 2003, 5, 2145. (d) Ma, S.; Hou, H.; Zhao, S.; Wang, G. Synthesis 2002, 1643. (e) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (f) Inoue, H.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. Tetrahedron 2002, 58, 83. (g) Satoh, T.; Sakamoto, T.; Watanabe, M. Tetrahedron Lett. 2002, 43, 2043. (h) Prabharasuth, R.; Van Vranken, D. L. J. Org. Chem. 2001, 66, 5256. (i) Hamada, T.; Mizojiri, R.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2000, 722, 7138. (j) Tius, M. A.; Pal, S. K. Tetrahedron Lett. 2001, 42, 2605. (k) Silveira, C. C.; Boeck, P.; Braga, A. L. Tetrahedron Lett. 2000, 41, 1867.
5. For some approaches to the synthesis of allenes, see: (a) Huang, X.; Xiong, Z.-C. Chem. Commun. 2003, 1714. (b) Huang, X.; Xiong, Z.-C. Tetrahedron Lett. 2003, 44, 5913. (c) Fukuhara, K.; Okamoto, S.; Sato, F. Org. Lett. 2003, 5, 2145. (d) Ma, S.; Hou, H.; Zhao, S.; Wang, G. Synthesis 2002, 1643. (e) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (f) Inoue, H.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. Tetrahedron 2002, 58, 83. (g) Satoh, T.; Sakamoto, T.; Watanabe, M. Tetrahedron Lett. 2002, 43, 2043. (h) Prabharasuth, R.; Van Vranken, D. L. J. Org. Chem. 2001, 66, 5256. (i) Hamada, T.; Mizojiri, R.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2000, 722, 7138. (j) Tius, M. A.; Pal, S. K. Tetrahedron Lett. 2001, 42, 2605. (k) Silveira, C. C.; Boeck, P.; Braga, A. L. Tetrahedron Lett. 2000, 41, 1867.
6. For some approaches to the synthesis of allenes, see: (a) Huang, X.; Xiong, Z.-C. Chem. Commun. 2003, 1714. (b) Huang, X.; Xiong, Z.-C. Tetrahedron Lett. 2003, 44, 5913. (c) Fukuhara, K.; Okamoto, S.; Sato, F. Org. Lett. 2003, 5, 2145. (d) Ma, S.; Hou, H.; Zhao, S.; Wang, G. Synthesis 2002, 1643. (e) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (f) Inoue, H.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. Tetrahedron 2002, 58, 83. (g) Satoh, T.; Sakamoto, T.; Watanabe, M. Tetrahedron Lett. 2002, 43, 2043. (h) Prabharasuth, R.; Van Vranken, D. L. J. Org. Chem. 2001, 66, 5256. (i) Hamada, T.; Mizojiri, R.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2000, 722, 7138. (j) Tius, M. A.; Pal, S. K. Tetrahedron Lett. 2001, 42, 2605. (k) Silveira, C. C.; Boeck, P.; Braga, A. L. Tetrahedron Lett. 2000, 41, 1867.
7. For some approaches to the synthesis of allenes, see: (a) Huang, X.; Xiong, Z.-C. Chem. Commun. 2003, 1714. (b) Huang, X.; Xiong, Z.-C. Tetrahedron Lett. 2003, 44, 5913. (c) Fukuhara, K.; Okamoto, S.; Sato, F. Org. Lett. 2003, 5, 2145. (d) Ma, S.; Hou, H.; Zhao, S.; Wang, G. Synthesis 2002, 1643. (e) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (f) Inoue, H.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. Tetrahedron 2002, 58, 83. (g) Satoh, T.; Sakamoto, T.; Watanabe, M. Tetrahedron Lett. 2002, 43, 2043. (h) Prabharasuth, R.; Van Vranken, D. L. J. Org. Chem. 2001, 66, 5256. (i) Hamada, T.; Mizojiri, R.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2000, 722, 7138. (j) Tius, M. A.; Pal, S. K. Tetrahedron Lett. 2001, 42, 2605. (k) Silveira, C. C.; Boeck, P.; Braga, A. L. Tetrahedron Lett. 2000, 41, 1867.
8. For some approaches to the synthesis of allenes, see: (a) Huang, X.; Xiong, Z.-C. Chem. Commun. 2003, 1714. (b) Huang, X.; Xiong, Z.-C. Tetrahedron Lett. 2003, 44, 5913. (c) Fukuhara, K.; Okamoto, S.; Sato, F. Org. Lett. 2003, 5, 2145. (d) Ma, S.; Hou, H.; Zhao, S.; Wang, G. Synthesis 2002, 1643. (e) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (f) Inoue, H.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. Tetrahedron 2002, 58, 83. (g) Satoh, T.; Sakamoto, T.; Watanabe, M. Tetrahedron Lett. 2002, 43, 2043. (h) Prabharasuth, R.; Van Vranken, D. L. J. Org. Chem. 2001, 66, 5256. (i) Hamada, T.; Mizojiri, R.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2000, 722, 7138. (j) Tius, M. A.; Pal, S. K. Tetrahedron Lett. 2001, 42, 2605. (k) Silveira, C. C.; Boeck, P.; Braga, A. L. Tetrahedron Lett. 2000, 41, 1867.
9. For some approaches to the synthesis of allenes, see: (a) Huang, X.; Xiong, Z.-C. Chem. Commun. 2003, 1714. (b) Huang, X.; Xiong, Z.-C. Tetrahedron Lett. 2003, 44, 5913. (c) Fukuhara, K.; Okamoto, S.; Sato, F. Org. Lett. 2003, 5, 2145. (d) Ma, S.; Hou, H.; Zhao, S.; Wang, G. Synthesis 2002, 1643. (e) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (f) Inoue, H.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. Tetrahedron 2002, 58, 83. (g) Satoh, T.; Sakamoto, T.; Watanabe, M. Tetrahedron Lett. 2002, 43, 2043. (h) Prabharasuth, R.; Van Vranken, D. L. J. Org. Chem. 2001, 66, 5256. (i) Hamada, T.; Mizojiri, R.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2000, 722, 7138. (j) Tius, M. A.; Pal, S. K. Tetrahedron Lett. 2001, 42, 2605. (k) Silveira, C. C.; Boeck, P.; Braga, A. L. Tetrahedron Lett. 2000, 41, 1867.
10. For some approaches to the synthesis of allenes, see: (a) Huang, X.; Xiong, Z.-C. Chem. Commun. 2003, 1714. (b) Huang, X.; Xiong, Z.-C. Tetrahedron Lett. 2003, 44, 5913. (c) Fukuhara, K.; Okamoto, S.; Sato, F. Org. Lett. 2003, 5, 2145. (d) Ma, S.; Hou, H.; Zhao, S.; Wang, G. Synthesis 2002, 1643. (e) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (f) Inoue, H.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. Tetrahedron 2002, 58, 83. (g) Satoh, T.; Sakamoto, T.; Watanabe, M. Tetrahedron Lett. 2002, 43, 2043. (h) Prabharasuth, R.; Van Vranken, D. L. J. Org. Chem. 2001, 66, 5256. (i) Hamada, T.; Mizojiri, R.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2000, 722, 7138. (j) Tius, M. A.; Pal, S. K. Tetrahedron Lett. 2001, 42, 2605. (k) Silveira, C. C.; Boeck, P.; Braga, A. L. Tetrahedron Lett. 2000, 41, 1867.
11. For some approaches to the synthesis of allenes, see: (a) Huang, X.; Xiong, Z.-C. Chem. Commun. 2003, 1714. (b) Huang, X.; Xiong, Z.-C. Tetrahedron Lett. 2003, 44, 5913. (c) Fukuhara, K.; Okamoto, S.; Sato, F. Org. Lett. 2003, 5, 2145. (d) Ma, S.; Hou, H.; Zhao, S.; Wang, G. Synthesis 2002, 1643. (e) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (f) Inoue, H.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. Tetrahedron 2002, 58, 83. (g) Satoh, T.; Sakamoto, T.; Watanabe, M. Tetrahedron Lett. 2002, 43, 2043. (h) Prabharasuth, R.; Van Vranken, D. L. J. Org. Chem. 2001, 66, 5256. (i) Hamada, T.; Mizojiri, R.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2000, 722, 7138. (j) Tius, M. A.; Pal, S. K. Tetrahedron Lett. 2001, 42, 2605. (k) Silveira, C. C.; Boeck, P.; Braga, A. L. Tetrahedron Lett. 2000, 41, 1867.
12. For some approaches to the synthesis of allenes, see: (a) Huang, X.; Xiong, Z.-C. Chem. Commun. 2003, 1714. (b) Huang, X.; Xiong, Z.-C. Tetrahedron Lett. 2003, 44, 5913. (c) Fukuhara, K.; Okamoto, S.; Sato, F. Org. Lett. 2003, 5, 2145. (d) Ma, S.; Hou, H.; Zhao, S.; Wang, G. Synthesis 2002, 1643. (e) Bacci, J. P.; Greenman, K. L.; Van Vranken, D. L. J. Org. Chem. 2003, 68, 4955. (f) Inoue, H.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. Tetrahedron 2002, 58, 83. (g) Satoh, T.; Sakamoto, T.; Watanabe, M. Tetrahedron Lett. 2002, 43, 2043. (h) Prabharasuth, R.; Van Vranken, D. L. J. Org. Chem. 2001, 66, 5256. (i) Hamada, T.; Mizojiri, R.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2000, 722, 7138. (j) Tius, M. A.; Pal, S. K. Tetrahedron Lett. 2001, 42, 2605. (k) Silveira, C. C.; Boeck, P.; Braga, A. L. Tetrahedron Lett. 2000, 41, 1867.
13. For some approaches to the asymmetric synthesis of allenes, see: (a) Hoffmann-Röder, A.; Krause, N. Angew. Chem. Int. Ed. 2002, 41, 2933. (b) Schultz-Fademrecht, C.; Wibbeling, B.; Fröhlich, R.; Hoppe, D. Org. Lett. 2001, 3, 1221. (c) Alexakis, A.; Mangeney, P.; Ghribi, A.; Marek, I.; Sedrani, R.; Guir, C.; Normant, J. F. Pure Appl. Chem. 1983, 60, 49. (d) Konoike, T.; Araki, Y. Tetrahedron Lett. 1992, 33, 5093. (e) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A.; Tracey, M. R. Org. Lett. 2003, 5, 2663. (f) Ogasawara, M.; Ueyama, K.; Nagano, T.; Mizuhata, Y.; Hayashi, T. Org. Lett. 2003, 5, 217. (g) Satoh, T.; Hanaki, N.; Kuramochi, Y.; Inoue, Y.; Hosoya, K.; Sakai, K. Tetrahedron 2002, 58, 2533. (h) Spino, C.; Fréchette, S. Tetrahedron Lett. 2000, 41, 8033. (i) Noguchi, Y.; Takiyama, H.; Katsuki, T. Synlett 1998, 543. (j) Mikami, K.; Yoshida, A. Angew. Chem. Int. Ed. Engl. 1997, 36, 858.
14. For some approaches to the asymmetric synthesis of allenes, see: (a) Hoffmann-Röder, A.; Krause, N. Angew. Chem. Int. Ed. 2002, 41, 2933. (b) Schultz-Fademrecht, C.; Wibbeling, B.; Fröhlich, R.; Hoppe, D. Org. Lett. 2001, 3, 1221. (c) Alexakis, A.; Mangeney, P.; Ghribi, A.; Marek, I.; Sedrani, R.; Guir, C.; Normant, J. F. Pure Appl. Chem. 1983, 60, 49. (d) Konoike, T.; Araki, Y. Tetrahedron Lett. 1992, 33, 5093. (e) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A.; Tracey, M. R. Org. Lett. 2003, 5, 2663. (f) Ogasawara, M.; Ueyama, K.; Nagano, T.; Mizuhata, Y.; Hayashi, T. Org. Lett. 2003, 5, 217. (g) Satoh, T.; Hanaki, N.; Kuramochi, Y.; Inoue, Y.; Hosoya, K.; Sakai, K. Tetrahedron 2002, 58, 2533. (h) Spino, C.; Fréchette, S. Tetrahedron Lett. 2000, 41, 8033. (i) Noguchi, Y.; Takiyama, H.; Katsuki, T. Synlett 1998, 543. (j) Mikami, K.; Yoshida, A. Angew. Chem. Int. Ed. Engl. 1997, 36, 858.
15. For some approaches to the asymmetric synthesis of allenes, see: (a) Hoffmann-Röder, A.; Krause, N. Angew. Chem. Int. Ed. 2002, 41, 2933. (b) Schultz-Fademrecht, C.; Wibbeling, B.; Fröhlich, R.; Hoppe, D. Org. Lett. 2001, 3, 1221. (c) Alexakis, A.; Mangeney, P.; Ghribi, A.; Marek, I.; Sedrani, R.; Guir, C.; Normant, J. F. Pure Appl. Chem. 1983, 60, 49. (d) Konoike, T.; Araki, Y. Tetrahedron Lett. 1992, 33, 5093. (e) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A.; Tracey, M. R. Org. Lett. 2003, 5, 2663. (f) Ogasawara, M.; Ueyama, K.; Nagano, T.; Mizuhata, Y.; Hayashi, T. Org. Lett. 2003, 5, 217. (g) Satoh, T.; Hanaki, N.; Kuramochi, Y.; Inoue, Y.; Hosoya, K.; Sakai, K. Tetrahedron 2002, 58, 2533. (h) Spino, C.; Fréchette, S. Tetrahedron Lett. 2000, 41, 8033. (i) Noguchi, Y.; Takiyama, H.; Katsuki, T. Synlett 1998, 543. (j) Mikami, K.; Yoshida, A. Angew. Chem. Int. Ed. Engl. 1997, 36, 858.
16. For some approaches to the asymmetric synthesis of allenes, see: (a) Hoffmann-Röder, A.; Krause, N. Angew. Chem. Int. Ed. 2002, 41, 2933. (b) Schultz-Fademrecht, C.; Wibbeling, B.; Fröhlich, R.; Hoppe, D. Org. Lett. 2001, 3, 1221. (c) Alexakis, A.; Mangeney, P.; Ghribi, A.; Marek, I.; Sedrani, R.; Guir, C.; Normant, J. F. Pure Appl. Chem. 1983, 60, 49. (d) Konoike, T.; Araki, Y. Tetrahedron Lett. 1992, 33, 5093. (e) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A.; Tracey, M. R. Org. Lett. 2003, 5, 2663. (f) Ogasawara, M.; Ueyama, K.; Nagano, T.; Mizuhata, Y.; Hayashi, T. Org. Lett. 2003, 5, 217. (g) Satoh, T.; Hanaki, N.; Kuramochi, Y.; Inoue, Y.; Hosoya, K.; Sakai, K. Tetrahedron 2002, 58, 2533. (h) Spino, C.; Fréchette, S. Tetrahedron Lett. 2000, 41, 8033. (i) Noguchi, Y.; Takiyama, H.; Katsuki, T. Synlett 1998, 543. (j) Mikami, K.; Yoshida, A. Angew. Chem. Int. Ed. Engl. 1997, 36, 858.
17. For some approaches to the asymmetric synthesis of allenes, see: (a) Hoffmann-Röder, A.; Krause, N. Angew. Chem. Int. Ed. 2002, 41, 2933. (b) Schultz-Fademrecht, C.; Wibbeling, B.; Fröhlich, R.; Hoppe, D. Org. Lett. 2001, 3, 1221. (c) Alexakis, A.; Mangeney, P.; Ghribi, A.; Marek, I.; Sedrani, R.; Guir, C.; Normant, J. F. Pure Appl. Chem. 1983, 60, 49. (d) Konoike, T.; Araki, Y. Tetrahedron Lett. 1992, 33, 5093. (e) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A.; Tracey, M. R. Org. Lett. 2003, 5, 2663. (f) Ogasawara, M.; Ueyama, K.; Nagano, T.; Mizuhata, Y.; Hayashi, T. Org. Lett. 2003, 5, 217. (g) Satoh, T.; Hanaki, N.; Kuramochi, Y.; Inoue, Y.; Hosoya, K.; Sakai, K. Tetrahedron 2002, 58, 2533. (h) Spino, C.; Fréchette, S. Tetrahedron Lett. 2000, 41, 8033. (i) Noguchi, Y.; Takiyama, H.; Katsuki, T. Synlett 1998, 543. (j) Mikami, K.; Yoshida, A. Angew. Chem. Int. Ed. Engl. 1997, 36, 858.
18. For some approaches to the asymmetric synthesis of allenes, see: (a) Hoffmann-Röder, A.; Krause, N. Angew. Chem. Int. Ed. 2002, 41, 2933. (b) Schultz-Fademrecht, C.; Wibbeling, B.; Fröhlich, R.; Hoppe, D. Org. Lett. 2001, 3, 1221. (c) Alexakis, A.; Mangeney, P.; Ghribi, A.; Marek, I.; Sedrani, R.; Guir, C.; Normant, J. F. Pure Appl. Chem. 1983, 60, 49. (d) Konoike, T.; Araki, Y. Tetrahedron Lett. 1992, 33, 5093. (e) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A.; Tracey, M. R. Org. Lett. 2003, 5, 2663. (f) Ogasawara, M.; Ueyama, K.; Nagano, T.; Mizuhata, Y.; Hayashi, T. Org. Lett. 2003, 5, 217. (g) Satoh, T.; Hanaki, N.; Kuramochi, Y.; Inoue, Y.; Hosoya, K.; Sakai, K. Tetrahedron 2002, 58, 2533. (h) Spino, C.; Fréchette, S. Tetrahedron Lett. 2000, 41, 8033. (i) Noguchi, Y.; Takiyama, H.; Katsuki, T. Synlett 1998, 543. (j) Mikami, K.; Yoshida, A. Angew. Chem. Int. Ed. Engl. 1997, 36, 858.
19. For some approaches to the asymmetric synthesis of allenes, see: (a) Hoffmann-Röder, A.; Krause, N. Angew. Chem. Int. Ed. 2002, 41, 2933. (b) Schultz-Fademrecht, C.; Wibbeling, B.; Fröhlich, R.; Hoppe, D. Org. Lett. 2001, 3, 1221. (c) Alexakis, A.; Mangeney, P.; Ghribi, A.; Marek, I.; Sedrani, R.; Guir, C.; Normant, J. F. Pure Appl. Chem. 1983, 60, 49. (d) Konoike, T.; Araki, Y. Tetrahedron Lett. 1992, 33, 5093. (e) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A.; Tracey, M. R. Org. Lett. 2003, 5, 2663. (f) Ogasawara, M.; Ueyama, K.; Nagano, T.; Mizuhata, Y.; Hayashi, T. Org. Lett. 2003, 5, 217. (g) Satoh, T.; Hanaki, N.; Kuramochi, Y.; Inoue, Y.; Hosoya, K.; Sakai, K. Tetrahedron 2002, 58, 2533. (h) Spino, C.; Fréchette, S. Tetrahedron Lett. 2000, 41, 8033. (i) Noguchi, Y.; Takiyama, H.; Katsuki, T. Synlett 1998, 543. (j) Mikami, K.; Yoshida, A. Angew. Chem. Int. Ed. Engl. 1997, 36, 858.
20. For some approaches to the asymmetric synthesis of allenes, see: (a) Hoffmann-Röder, A.; Krause, N. Angew. Chem. Int. Ed. 2002, 41, 2933. (b) Schultz-Fademrecht, C.; Wibbeling, B.; Fröhlich, R.; Hoppe, D. Org. Lett. 2001, 3, 1221. (c) Alexakis, A.; Mangeney, P.; Ghribi, A.; Marek, I.; Sedrani, R.; Guir, C.; Normant, J. F. Pure Appl. Chem. 1983, 60, 49. (d) Konoike, T.; Araki, Y. Tetrahedron Lett. 1992, 33, 5093. (e) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A.; Tracey, M. R. Org. Lett. 2003, 5, 2663. (f) Ogasawara, M.; Ueyama, K.; Nagano, T.; Mizuhata, Y.; Hayashi, T. Org. Lett. 2003, 5, 217. (g) Satoh, T.; Hanaki, N.; Kuramochi, Y.; Inoue, Y.; Hosoya, K.; Sakai, K. Tetrahedron 2002, 58, 2533. (h) Spino, C.; Fréchette, S. Tetrahedron Lett. 2000, 41, 8033. (i) Noguchi, Y.; Takiyama, H.; Katsuki, T. Synlett 1998, 543. (j) Mikami, K.; Yoshida, A. Angew. Chem. Int. Ed. Engl. 1997, 36, 858.
21. For some approaches to the asymmetric synthesis of allenes, see: (a) Hoffmann-Röder, A.; Krause, N. Angew. Chem. Int. Ed. 2002, 41, 2933. (b) Schultz-Fademrecht, C.; Wibbeling, B.; Fröhlich, R.; Hoppe, D. Org. Lett. 2001, 3, 1221. (c) Alexakis, A.; Mangeney, P.; Ghribi, A.; Marek, I.; Sedrani, R.; Guir, C.; Normant, J. F. Pure Appl. Chem. 1983, 60, 49. (d) Konoike, T.; Araki, Y. Tetrahedron Lett. 1992, 33, 5093. (e) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A.; Tracey, M. R. Org. Lett. 2003, 5, 2663. (f) Ogasawara, M.; Ueyama, K.; Nagano, T.; Mizuhata, Y.; Hayashi, T. Org. Lett. 2003, 5, 217. (g) Satoh, T.; Hanaki, N.; Kuramochi, Y.; Inoue, Y.; Hosoya, K.; Sakai, K. Tetrahedron 2002, 58, 2533. (h) Spino, C.; Fréchette, S. Tetrahedron Lett. 2000, 41, 8033. (i) Noguchi, Y.; Takiyama, H.; Katsuki, T. Synlett 1998, 543. (j) Mikami, K.; Yoshida, A. Angew. Chem. Int. Ed. Engl. 1997, 36, 858.
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