Mukaiyama-Michael reaction of cyclic ketene silyl acetals and enones. Importance of ring flexibility in electron transfer process

Tetrahedron Letters

Volumn 38, Issue 12, 1997, Pages 2117-2120

  Fujita, Yukihiro ^a   Fukuzumi, Shunichi ^b   Otera, Junzo ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; MACROCYCLIC COMPOUND;

ARTICLE; CHEMICAL REACTION; CONFORMATION; DRUG SYNTHESIS; ELECTRON TRANSPORT;

EID: 0031585086     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00321-3     Document Type: Article

References (9)

1. 1. Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H.; Fukuzumi, S. J. Am. Chem. Soc. 1991, 113, 4028.
2. 2. Otera, J.; Fujita, Y.; Sato, T.; Nozaki, H.; Fukuzumi, S.; Fujita, M. J. Org. Chem. 1992, 57, 5054.
3. 3. Fukuzumi, S.; Fujita, M.; Otera, J.; Fujita, Y. J. Am. Chem. Soc. 1992, 114, 10271.
4. 4. Otera, J.; Fujita, Y.; Sakuta, N.; Fujita, M.; Fukuzumi, S. J. Org. Chem. 1996, 61, 2951.
5. 5. Dale, J.; Top. Stereochem. 1976, 9, 199. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; John Wiley & Sons, INC.: New York, 1994; Chapter 11.
6. 5. Dale, J.; Top. Stereochem. 1976, 9, 199. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; John Wiley & Sons, INC.: New York, 1994; Chapter 11.
7. 6. The macrocyclic enones were prepared according to the following method: (equation presented) (a) Evans, D. A.; Longmire, J. M.; Modi, D. P. Tetrahedron Lett. 1995, 36, 3985.
8. (b) Binkley, E. S.; Heathcock, C. H. J. Org. Chem. 1975, 40, 2156.
9. (c) Ryu, I.; Hatayama, Y.; Sonoda, N. Tetrahedron Lett. 1978, 3455. We obtained a single isomer but the geometry of the double bond was not assigned although the E-geometry is highly conceivable.