Pd(0)-catalyzed insertion-cyclization reaction of 2,3-allenols with aryl or alkenyl halides. Diastereoselective synthesis of highly optically active trans-2,3-disubstituted vinylic oxiranes [7]

Journal of the American Chemical Society

Volumn 121, Issue 34, 1999, Pages 7943-7944

  Ma, Shengming ^a   Zhao, Shimin ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; EPOXIDE; ETHYLENE OXIDE DERIVATIVE; HALOGENATED HYDROCARBON; PALLADIUM; VINYL DERIVATIVE;

CATALYST; CYCLIZATION; DIASTEREOISOMER; LETTER; OPTICAL ROTATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033199978     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9904888     Document Type: Letter

References (29)

1. Schuster, H. F.; Coppola, G. M. Allenes in Organic Synthesis; John Wiley & Sons: New York, 1988. The Chemistry of Ketenes, Allenes, and Related Compounds; Patai, S., Ed.; John Wiley & Sons: New York, 1980; Part 1.
2. Schuster, H. F.; Coppola, G. M. Allenes in Organic Synthesis; John Wiley & Sons: New York, 1988. The Chemistry of Ketenes, Allenes, and Related Compounds; Patai, S., Ed.; John Wiley & Sons: New York, 1980; Part 1.
3. Walkup, R. D.; Kim, S. W.; Wagy, S. D. J. Org. Chem. 1993, 58, 6486. Fox, D. N. A.; Lathbury, D.; Mahon, M. F.; Malloy, K. C.; Gallagher, T. J. Am. Chem. Soc. 1991, 113, 2652. Kimura, M.; Fugami, K.; Tanaka, S.; Tamara, Y. J. Org. Chem. 1992, 57, 6377. Yamamoto, Y. Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. Trost, B.; Gerusz, V. J. Am. Chem. Soc. 1995, 117, 5156.
4. Walkup, R. D.; Kim, S. W.; Wagy, S. D. J. Org. Chem. 1993, 58, 6486. Fox, D. N. A.; Lathbury, D.; Mahon, M. F.; Malloy, K. C.; Gallagher, T. J. Am. Chem. Soc. 1991, 113, 2652. Kimura, M.; Fugami, K.; Tanaka, S.; Tamara, Y. J. Org. Chem. 1992, 57, 6377. Yamamoto, Y. Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. Trost, B.; Gerusz, V. J. Am. Chem. Soc. 1995, 117, 5156.
5. Walkup, R. D.; Kim, S. W.; Wagy, S. D. J. Org. Chem. 1993, 58, 6486. Fox, D. N. A.; Lathbury, D.; Mahon, M. F.; Malloy, K. C.; Gallagher, T. J. Am. Chem. Soc. 1991, 113, 2652. Kimura, M.; Fugami, K.; Tanaka, S.; Tamara, Y. J. Org. Chem. 1992, 57, 6377. Yamamoto, Y. Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. Trost, B.; Gerusz, V. J. Am. Chem. Soc. 1995, 117, 5156.
6. Walkup, R. D.; Kim, S. W.; Wagy, S. D. J. Org. Chem. 1993, 58, 6486. Fox, D. N. A.; Lathbury, D.; Mahon, M. F.; Malloy, K. C.; Gallagher, T. J. Am. Chem. Soc. 1991, 113, 2652. Kimura, M.; Fugami, K.; Tanaka, S.; Tamara, Y. J. Org. Chem. 1992, 57, 6377. Yamamoto, Y. Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. Trost, B.; Gerusz, V. J. Am. Chem. Soc. 1995, 117, 5156.
7. Walkup, R. D.; Kim, S. W.; Wagy, S. D. J. Org. Chem. 1993, 58, 6486. Fox, D. N. A.; Lathbury, D.; Mahon, M. F.; Malloy, K. C.; Gallagher, T. J. Am. Chem. Soc. 1991, 113, 2652. Kimura, M.; Fugami, K.; Tanaka, S.; Tamara, Y. J. Org. Chem. 1992, 57, 6377. Yamamoto, Y. Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. Trost, B.; Gerusz, V. J. Am. Chem. Soc. 1995, 117, 5156.
8. For some of our recent results in allenes, see: (a) Ma, S.; Shi, Z.; Li, L. J. Org. Chem. 1998, 63, 4522. (b) Ma, S.; Wei, Q. J. Org. Chem. 1999, 64, 1026. (c) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387.
9. For some of our recent results in allenes, see: (a) Ma, S.; Shi, Z.; Li, L. J. Org. Chem. 1998, 63, 4522. (b) Ma, S.; Wei, Q. J. Org. Chem. 1999, 64, 1026. (c) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387.
10. For some of our recent results in allenes, see: (a) Ma, S.; Shi, Z.; Li, L. J. Org. Chem. 1998, 63, 4522. (b) Ma, S.; Wei, Q. J. Org. Chem. 1999, 64, 1026. (c) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387.
11. Olsson, L.-I.; Claesson, A. Synthesis 1979, 743.
12. Marshall, J. A.; Pinney, K. G. J. Org. Chem. 1993, 58, 7180. Marshall, J. A.; Yu, R. H.; Perkins, J. F. J. Org. Chem. 1995, 60, 5550.
13. Marshall, J. A.; Pinney, K. G. J. Org. Chem. 1993, 58, 7180. Marshall, J. A.; Yu, R. H.; Perkins, J. F. J. Org. Chem. 1995, 60, 5550.
14. Shimizu, I.; Sugiura, T.; Tsuji, J. J. Org. Chem. 1985, 50, 537.
15. Olsson, L.-I.; Claesson, A.; Bogentoft, C. Acta Chem. Scand 1974, 28, 765.
16. Maruoka, K.; Hasegawa, M.; Yamamoto, H. J. Am. Chem. Soc. 1986, 108, 3827. Maruoka, K.; Ooi, T.; M.; Yamamoto, H. J. Am. Chem. Soc. 1989, 111, 6431. Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1993, 115, 12208.
17. Maruoka, K.; Hasegawa, M.; Yamamoto, H. J. Am. Chem. Soc. 1986, 108, 3827. Maruoka, K.; Ooi, T.; M.; Yamamoto, H. J. Am. Chem. Soc. 1989, 111, 6431. Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1993, 115, 12208.
18. Maruoka, K.; Hasegawa, M.; Yamamoto, H. J. Am. Chem. Soc. 1986, 108, 3827. Maruoka, K.; Ooi, T.; M.; Yamamoto, H. J. Am. Chem. Soc. 1989, 111, 6431. Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1993, 115, 12208.
19. Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7379.
20. Nishizawa, M.; Yamada, M.; Noyori, R. Tetrahedron Lett. 1981, 22, 247.
21. %ee was determined by HPLC with a CHIRALPAK AD column (φ 0.46 cm × 25 cm from Daicel Chemical Ind., Ltd.).
22. According to Corey's method, chiral 2,3-dienols can be synthesized in one step via the reaction of aldehydes with chiral borane reagents. This makes our methodology highly attractive. Corey, E. J.; Yu, C-M.; Lee, D.-H. J. Am. Chem. Soc. 1990, 112, 878.
23. (a) For a seminal paper of the asymmetric Sharpless epoxidation reaction of allylic alcohols, see: Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974. (b) For kinetic resolution of racemic allylic alcohols, see: Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237.
24. (a) For a seminal paper of the asymmetric Sharpless epoxidation reaction of allylic alcohols, see: Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974. (b) For kinetic resolution of racemic allylic alcohols, see: Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237.
25. For kinetic resolution of racemic terminal oxiranes, see: Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936.
26. For some of the most recent advances in the asymmetric epoxidation of simple alkenes, see: Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. Irie, R.; Noda, K.; Ito, Y.; Matsumoto, N.; Katsuki, K. Tetrahedron Lett. 1990, 31, 7345. Tu, Y.; Wang, Z.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. Yang, D.; Yip, Y.; Tang, M.; Wong, M.; Zheng, J.; Cheung, K. J. Am. Chem. Soc. 1996, 118, 491.
27. For some of the most recent advances in the asymmetric epoxidation of simple alkenes, see: Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. Irie, R.; Noda, K.; Ito, Y.; Matsumoto, N.; Katsuki, K. Tetrahedron Lett. 1990, 31, 7345. Tu, Y.; Wang, Z.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. Yang, D.; Yip, Y.; Tang, M.; Wong, M.; Zheng, J.; Cheung, K. J. Am. Chem. Soc. 1996, 118, 491.
28. For some of the most recent advances in the asymmetric epoxidation of simple alkenes, see: Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. Irie, R.; Noda, K.; Ito, Y.; Matsumoto, N.; Katsuki, K. Tetrahedron Lett. 1990, 31, 7345. Tu, Y.; Wang, Z.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. Yang, D.; Yip, Y.; Tang, M.; Wong, M.; Zheng, J.; Cheung, K. J. Am. Chem. Soc. 1996, 118, 491.
29. For some of the most recent advances in the asymmetric epoxidation of simple alkenes, see: Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801. Irie, R.; Noda, K.; Ito, Y.; Matsumoto, N.; Katsuki, K. Tetrahedron Lett. 1990, 31, 7345. Tu, Y.; Wang, Z.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. Yang, D.; Yip, Y.; Tang, M.; Wong, M.; Zheng, J.; Cheung, K. J. Am. Chem. Soc. 1996, 118, 491.