Multinuclear Pd/Zn complex-catalyzed asymmetric alkylative ring-opening reaction of oxabicyclic alkenes

Organic Letters

Volumn 13, Issue 5, 2011, Pages 868-871

  Endo, Kohei ^a   Tanaka, Keisuke ^b   Ogawa, Mika ^b   Shibata, Takanori ^b  

^a WASEDA UNIVERSITY   (Japan)

^b WASEDA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79952150597     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102928q     Document Type: Article

References (27)

1. Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187
2. Majima, K.; Takita, R.; Okada, A.; Oshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 15837
3. Matsunaga, S.; Yoshida, T.; Morimoto, H.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8777
4. Takacs, J. M.; Reddy, D. S.; Moteki, S. A.; Wu, D.; Palencia, H. J. Am. Chem. Soc. 2004, 126, 4494
5. Shibasaki, M.; Matsunaga, S. Chem. Soc. Rev. 2006, 35, 269
6. Chen, Z.; Morimoto, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2008, 130, 2170
7. Trost, B. M.; Müller, C. J. Am. Chem. Soc. 2008, 130, 2438
8. Shibasaki, M.; Kanai, M.; Matsunaga, S.; Kumagai, N. Acc. Chem. Res. 2009, 42, 1117 and references therein
9. Endo, K.; Ogawa, M.; Shibata, T. Angew. Chem., Int. Ed. 2010, 49, 2410
10. For reviews, see: Lautens, M. Synlett 1993, 177
11. Chiu, P.; Lautens, M. Top. Curr. Chem. 1997, 190, 1
12. Lautens, M.; Fagnou, K.; Hiebert, S. Acc. Chem. Res. 2003, 36, 48
13. Lautens, M.; Renaud, J.-L.; Hiebert, S. J. Am. Chem. Soc. 2000, 122, 1804
14. Lautens, M.; Hiebert, S.; Renaud, J.-L. Org. Lett. 2000, 2, 1971
15. Lautens, M.; Hiebert, S.; Renaud, J.-L. J. Am. Chem. Soc. 2001, 123, 6834
16. Priego, J.; Mancheño, O. G.; Cabrera, S.; Arrayás, R. G.; Llamas, T.; Carretero, J. C. Chem. Commun. 2002, 2512
17. Lautens, M.; Hiebert, S. J. Am. Chem. Soc. 2004, 126, 1437
18. Dotta, P.; Kumar, P. G. A.; Pregosin, P. S.; Albinati, A.; Rizzato, S. Organometallics 2004, 23, 2295
19. Cabrera, S.; Arrayás, R. G.; Carretero, J. C. Angew. Chem., Int. Ed. 2004, 43, 3944
20. Imamoto, T.; Sugita, K.; Yoshida, K. J. Am. Chem. Soc. 2005, 127, 11934
21. Cabrera, S.; Arrayás, R. G.; Alonso, I.; Carretero, J. C. J. Am. Chem. Soc. 2005, 127, 17938
22. Imamoto, T.; Kumada, A.; Yoshida, K. Chem. Lett. 2007, 36, 500
23. Imamoto, T.; Saitoh, Y.; Koide, A.; Ogura, T.; Yoshida, K. Angew. Chem., Int. Ed. 2007, 46, 8636
24. Ogura, T.; Yoshida, K.; Yanagisawa, A.; Imamoto, T. Org. Lett. 2009, 11, 2245
25. (R)-BINOL (>99.0% ee) was purchased from Fuji Molecular Planning Co., Ltd. at JPY50,000/500 g.
26. 2Zn (3 equiv) gave the product in 21% yield with 13% ee. The details are under examination.
27. Almost no reaction occurred in a single solvent of hexane.