SmI2-Promoted conjugate reduction of α,β-unsaturated esters and ketones studied in comparison with Mukaiyama-Michael reaction of ketene silyl acetal

Tetrahedron Letters

Volumn 38, Issue 12, 1997, Pages 2121-2124

  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; ESTER; KETONE; MACROCYCLIC COMPOUND; SAMARIUM;

ARTICLE; CHEMICAL REACTION; CONJUGATION; DIMERIZATION; DRUG SYNTHESIS; ELECTRON TRANSPORT; REDUCTION;

EID: 0031585106     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00322-5     Document Type: Article

References (10)

1. 1. Inanaga, J.; Handa, Y.; Tabuchi, T.; Otsubo, K.; Yamagauchi, M.; Hanamoto, T. Tetrahedron Lett. 1991, 32, 6557.
2. 2. Inanaga, J.; Sasaki, S.; Handa, Y.; Yamaguchi, M.; Yokoyama, Y. Chem. Lett. 1991, 2117.
3. 3. Cabrera, A.; Alper, H. Tetrahedron Lett. 1992, 33, 5007.
4. 4. Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H.; Fukuzumi, S. J. Am. Chem. Soc. 1991, 113, 4028.
5. 5. Otera, J.; Fujita, Y.; Sato, T.; Nozaki, H.; Fukuzumi, S.; Fujita, M. J. Org. Chem. 1992, 57, 5054.
6. 6. Fukuzumi, S.; Fujita, M.; Otera, J.; Fujita, Y. J. Am. Chem. Soc. 1992, 114, 10271.
7. 7. Otera, J.; Fujita, Y.; Sakuta, N.; Fujita, M.; Fukuzumi, S. J. Org. Chem. 1996, 61, 2951.
8. 8. Fujita, Y.; Fukuzumi, S.; Otera, J. preceding paper in this issue.
9. 9. The macrocyclic lactone was prepared as follows: (equation presented) Cf: Trost, B. M.; Salzmann, T. N.; Hiroi, K. J. Am. Chem. Soc. 1976, 98, 4887.
10. 10. This is also the case for the acyclic enone. (equation presented)