Highly regio- and stereoselective acylboration of allenes catalyzed by palladium complexes: An efficient route to a new class of 2-acylallylboronates [5]

Journal of the American Chemical Society

Volumn 122, Issue 29, 2000, Pages 7122-7123

  Yang, Feng Yu ^a   Wu, Ming Yuan ^a   Cheng, Chien Hong ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; BORONIC ACID DERIVATIVE; PALLADIUM COMPLEX;

CATALYSIS; LETTER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; TECHNIQUE;

EID: 0034718084     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001082u     Document Type: Letter

References (31)

1. (a) Wang, Z.; Lu, X.; Lei, A.; Zhang, Z. J. Org. Chem. 1998, 63, 3806-3807.
2. (b) Chatani, N.; Amishiro, N.; Murai, S. J. Am. Chem. Soc. 1991, 113, 7778-7780.
3. (c) Ikeda, S. I.; Cui, D. M.; Sato, Y. J. Am. Chem. Soc. 1999, 121, 4712-4713.
4. (d) Nakamura, H.; Shim, J. G.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8113-8114.
5. (a) Wu, M. Y.; Yang, F. Y.; Cheng, C. H. J. Org. Chem. 1999, 64, 2471-2474.
6. (b) Yang, F. Y.; Wu, M. Y.; Cheng, C. H. Tetrahedron Lett. 1999, 40, 6055-6058.
7. (a) Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: New York, 1980.
8. (b) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994.
9. (a) Larock, R. C.; Tu, C.; Pace, P. J. Org. Chem. 1998, 63, 6859-6866.
10. (b) Larock, R. C.; He, Y.; Leng, W. W.; Han, X.; refvik, M. D.; Zenner, J. M. J. Org. Chem. 1998, 63, 2154-2160.
11. (c) Ma, S.; Negishi, E. I. J. Am. Chem. Soc. 1995, 117, 6345-6357.
12. (d) Gamex, P.; Ariente, C.; Gore, J.; Cazes, B. Tetrahedron 1998, 54, 14825-14834.
13. (e) Al-Masum, M.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 3809-3810.
14. (f) Jonasson, C. Backvall, J. E. Tetrahedron Lett. 1998, 39, 3601-3604.
15. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
16. (a) Vaultier, M.; Carboni, B. Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 11, p 191-276.
17. (b) Roush, W. R.; Grover, P. T. J. Org. Chem. 1995, 60, 3806-3813.
18. (c) Brown, H. C.; Ramachandran, P. V. Pure Appl. Chem. 1991, 63, 307-316.
19. (a) Obora, Y.; Tsuji, Y.; Kawamura, T. J. Am. Chem. Soc. 1993, 115, 10414-10415.
20. (b) Obara, Y.; Tsuji, Y.; Kawamura, T. J. Am. Chem. Soc. 1995, 115, 9814-9821.
21. Yamamoto, K.; Hayashi, A.; Suzuki, S.; Tsuji, J. Organometallics 1987, 6, 974-979.
22. (a) Grigg, R.; Brown, S.; Sridharan, V.; Uttley, M. D. Tetrahedron Lett. 1997, 38, 5031-5034.
23. (b) Okuro, K.; Alper, H. J. Org. Chem. 1997, 62, 1566-1567.
24. (a) Ishiyama, T.; Itoh, Y.; Kitano, T.; Miyaura, N. Tetrahedron Lett. 1997, 38, 3447-3450.
25. (b) Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508-7510.
26. (a) Ahiko, T. A.; Ishiyama, T.; Miyaura, N. Chem. Lett. 1997, 811-812.
27. (b) Ishiyama, T.; Ahiko, T.; Miyaura, N. Tetrahedron Lett. 1996, 37, 6889-6892.
28. (a) Ohno, K.; Tsuji, J. J. Am. Chem. Soc. 1968, 90, 99-107.
29. (b) Lau, K. S. Y.; Becker, Y.; Huang, F.; Baenziger, N.; Still, J. K. J. Am. Chem. Soc. 1977, 99, 5664-5672.
30. (c) Krafft, T. E.; Rich, J. D.; McDermott, P. J. J. Org. Chem. 1990, 55, 5430-5432.
31. (d) Rich, J. D. J. Am. Chem. Soc. 1989, 111, 5886-5893.