Reversal of Chemoselectivity in Organotin Lewis Acid-Catalyzed Reaction of Ketene Silyl Acetal with Aldehyde and α-Enal

Synlett

Volumn 1997, Issue 1, 1997, Pages 29-30

  Chen, Jianxie ^a   Otera, Junzo ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003831823     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-715     Document Type: Article

References (12)

1. Sato, T.; Otera, J.; Nozaki, H J. Org. Chem. 1993, 58, 4971, and references cited therein.
2. Reetz, M. T. "Organotitanium Reagents in Organic Synthesis", Springer-Verlag, Berlin, 1986, Chapter 3.
3. Markó, I. E.; Leung, C. W. J . Am. Chem. Soc. 1994, 116, 371.
4. Sato, T.; Otera, J.; Nozaki, H. J. Am. Chem. Soc. 1990, 112, 901. Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. Tetrahedron Lett. 1990, 31, 1581. Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. J. Am. Chem. Soc. 1991, 113, 4028. Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. Tetrahedron 1991, 47, 9773. Otera, J.; Chen. J. Synlett 1996, 321. Chen, J.; Sakamoto, M.; Orita, A.; Otera, J. Synlett 1996, 877.
5. Sato, T.; Otera, J.; Nozaki, H. J. Am. Chem. Soc. 1990, 112, 901. Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. Tetrahedron Lett. 1990, 31, 1581. Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. J. Am. Chem. Soc. 1991, 113, 4028. Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. Tetrahedron 1991, 47, 9773. Otera, J.; Chen. J. Synlett 1996, 321. Chen, J.; Sakamoto, M.; Orita, A.; Otera, J. Synlett 1996, 877.
6. Sato, T.; Otera, J.; Nozaki, H. J. Am. Chem. Soc. 1990, 112, 901. Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. Tetrahedron Lett. 1990, 31, 1581. Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. J. Am. Chem. Soc. 1991, 113, 4028. Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. Tetrahedron 1991, 47, 9773. Otera, J.; Chen. J. Synlett 1996, 321. Chen, J.; Sakamoto, M.; Orita, A.; Otera, J. Synlett 1996, 877.
7. Sato, T.; Otera, J.; Nozaki, H. J. Am. Chem. Soc. 1990, 112, 901. Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. Tetrahedron Lett. 1990, 31, 1581. Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. J. Am. Chem. Soc. 1991, 113, 4028. Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. Tetrahedron 1991, 47, 9773. Otera, J.; Chen. J. Synlett 1996, 321. Chen, J.; Sakamoto, M.; Orita, A.; Otera, J. Synlett 1996, 877.
8. Sato, T.; Otera, J.; Nozaki, H. J. Am. Chem. Soc. 1990, 112, 901. Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. Tetrahedron Lett. 1990, 31, 1581. Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. J. Am. Chem. Soc. 1991, 113, 4028. Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. Tetrahedron 1991, 47, 9773. Otera, J.; Chen. J. Synlett 1996, 321. Chen, J.; Sakamoto, M.; Orita, A.; Otera, J. Synlett 1996, 877.
9. Sato, T.; Otera, J.; Nozaki, H. J. Am. Chem. Soc. 1990, 112, 901. Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. Tetrahedron Lett. 1990, 31, 1581. Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. J. Am. Chem. Soc. 1991, 113, 4028. Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. Tetrahedron 1991, 47, 9773. Otera, J.; Chen. J. Synlett 1996, 321. Chen, J.; Sakamoto, M.; Orita, A.; Otera, J. Synlett 1996, 877.
10. 3-catalyzed reaction: Mikami, K.; Terada, M.; Nakai, T. J. Org. Chem. 1991, 56, 5456.
11. For comparison of acidity between tin and titanium Lewis acids: Otera, J.; Fujita, Y.; Sakuta, Y.; Fujita, M.; Fukuzumi, S. J. Org. Chem. 1996, 61, 2951.
12. More detailed discussion on this issue will be given by Nakai's group: Hanuyda, K.; Hirai, K.-i.; Nakai, T Synlett 1997, 31.