Tandem Mukaiyama Michael-aldol reactions catalyzed by samarium diiodide

Tetrahedron Letters

Volumn 39, Issue 43, 1998, Pages 7845-7848

  Giuseppone, Nicolas ^a   Courtaux, Yann ^a   Collin, Jacqueline ^a  

^a UFR des Sciences Exactes et Naturelles   (France)

Author keywords

Aldol reactions; Catalysis; Michael reactions; Samarium

Indexed keywords

IODINE DERIVATIVE; SAMARIUM;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE;

EID: 0032558609     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01724-9     Document Type: Article

References (15)

1. [1] Tietze, L.F. Chem. Rev. 1996, 96, 115-136.
2. [2] Denmark, S.E.; Thorarensen, A. Chem. Rev. 1996, 96, 137-165.
3. [3] Parsons, P.J.; Penkett, C.S.; Shell, A.J. Chem. Rev. 1996, 96, 195-206.
4. [4] Noyori, R.; Suzuki, M. Angew. Chem. Int. Ed. Engl. 1984, 23, 847-876.
5. [5] Marczak, S.; Michalak, K.; Urbanczyk-Lipkowska, Z.; Wicha, J. J. Org. Chem. 1998, 63, 2218-2223.
6. [6] Kobayashi, S.; Mukaiyama, T. Chem. Lett. 1986, 1805-1808.
7. [7] Kobayashi, S.; Mukaiyama, T. Chem. Lett. 1986, 221-224.
8. [8] Mukaiyama, T; Sagawa, Y.; Kobayashi, S. Chem. Lett. 1986, 1821-1824.
9. [9] Yamada, K.; Arai, T.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1998, 63, 3666-3672.
10. [10] Collin, J.; Giuseppone, N.; Van de Weghe, P. Coord. Chem. Rev. in press.
11. [11] Van de Weghe, P.; Collin, J. Tetrahedron Lett. 1993, 34, 3881-3884.
12. [12] Giuseppone, N.; Van de Weghe, P.; Mellah; M., Collin, J. Tetrahedron. submitted for publication.
13. 2 was added at the same temperature. The reaction mixture was allowed to stand at -60°C during 36 h. The reaction was stopped by the addition of hexane (40 mL) which precipitated the samarium salts. After filtration through celite the solvents were removed under reduced pressure and the product was purified by column chromatography on desactivated silica gel (527 mg, 70% yield).
14. 4Si: 376.2069, Found : 376.2070.
15. 3J H-H (J=0 for the two protons on the cycle, J=5.1 Hz corresponding to syn positions on the two other asymmetric carbons) and by 2D NMR experiments.