Tributylstannyl 4-tributylstannylbut-3-enoate: A useful C-4 homologating agent. Application to the synthesis of aryl iodolactones

Tetrahedron Letters

Volumn 37, Issue 42, 1996, Pages 7507-7510

  Thibonnet, Jérôme ^a   Abarbri, Mohamed ^a   Parrain, Jean Luc ^b   Duchêne, Alain ^a  

^a UNIVERSITÉ DE TOURS   (France)

^b AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE; ORGANOIODINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030583491     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01725-X     Document Type: Article

References (16)

1. 1. Duchêne, A.; Abarbri, M.; Parrain, J.-L. Tetrahedron Lett. 1995, 36, 2469-2472.
2. 2. Pereyre, M.; Quintard, J.-P.; Rahm, A. "Tin in Organic Synthesis", Butterworths, London 1987.
3. 3. Parrain, J.-L.; Duchêne, A.; Quintard, J.-P. J. Chem. Soc., Perkin Trans. 1 1990, 187-189.
4. 4. a) Quintard, J.-P.; Pereyre, M. J. Organomet. Chem. 1972, 42, 75-93.
5. b) Piers, E.; Chong, J.M.; Morton, H.E. Tetrahedron 1989, 45, 363-380.
6. 5. Parrain, J.-L. Duchêne, A.; Quintard, J.-P. Tetrahedron Lett. 1990, 31, 1857-1860.
7. 6. Leusink, A.J.; Budding, H.A. J. Organomet. Chem. 1968, 11, 533-535.
8. 7. Prevost, C.; Gaudemar, M.; Honiberg, J. C. R. Acad. Sci. 1950, 230, 1186-1188.
9. 8. Stille, J.K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
10. 3, 50 MHz) : 38.3, 101.5, 106, 108.7, 119.4, 121.4, 131.5, 133.9, 147.7; 148.4, 178.4. MS (70 eV): 206(M , 91), 161(32), 131(100), 103(85), 77(32), 51(15), 45(12).
11. 2 in DMF gave low to moderate conversion rates (<50%).
12. 11. Abarbri, M.; Parrain, J.-L.; Cintrat J.-C; Duchêne, A. Synthesis 1996, 82-86.
13. 12. Carter Royer, A.; Mebane, R.C.; Swafford, A.M. Synlett 1993, 899-900.
14. 13. Klix, R.C., Cain, M.H.; Bathia, A.V. Tetrahedron Lett. 1995, 36, 6413-6414 and ref. therein.
15. 14. Birch, A.J.; Williamson, D.H. Org. React. 1976, 24, 1-186.
16. 15. Acylation leads only to 4,5-methylenedioxy-1-tetralone.