First synthesis and crystal structures of chiral 1,3-dienylborates

Heterocycles

Volumn 50, Issue 2, 1999, Pages 703-711

  Mortier, Jacques ^a   Vaultier, Michel ^a   Plunian, Barbara ^a   Toupet, Loïc ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIENYLBORIC ACID; BORIC ACID; NITROGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; DIASTEREOISOMER; ENVIRONMENTAL TEMPERATURE; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY DIFFRACTION;

EID: 0033117366     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-98-S(H)60     Document Type: Article

References (30)

1. N. Farfán, L. Cuéllar, and J. M. Aceves, Synthesis, 1987, 927.
2. A. Correa, J.-N. Denis, and A. E. Greene, Synth. Commun., 1991, 21, 1.
3. Prepared by treatment of 2-methyl-3-butyn-2-ol with acetic anhydride (61%): L. Brandsma, 'Preparative Acetylenic Chemistry', Elsevier, Amsterdam.
4. M. Vaultier, F. Truchet, B. Carboni, R. W. Hoffmann, and I. Denne, Tetrahedron Lett., 1987, 28, 4169.
5. A number of stable stereogenic boron structures are known: (a) B. M. Mikhailov, T. V. Kostroma, and N. S. Fedotov, Izv. Akad. Nauk. SSSR, 1957, 598;
6. (b) E. Z. Hohaus, Anorg, Allg. Chem., 1982, 484, 41;
7. (c) B. Gyori and J. Emri, J. Organomet. Chem., 1982, 238, 159;
8. (d) T. Mancilla and R. Contreras, J. Organomet. Chem., 1987, 321, 191;
9. (e) H. C. Brown and A. K. Gupta, J. Organomet. Chem., 1988, 341, 73;
10. (f) W. Kliegel, M. Tajerbashi, S. J. Rettig, and J. Trotter, Can. J. Chem., 1989, 67, 1636;
11. (g) M. S. Korobov, G. S. Borodkin, N. Borisenko, T. A. Ryskina, L. E. Novorochkin, and V. I. Minkin, Theochem., 1989, 59, 61;
12. (h) W. Kliegel, U. Schumacher, S. J. Rettig, and J. Trotter, Can. J. Chem., 1992, 70, 1188;
13. (i) S. Toyota and M. Oki, Bull. Chem. Soc. Jpn., 1992, 65, 1832;
14. (j) E. Vedejs, S. C. Fields, S. Lin, and M. R. Schrimpf, J. Am. Chem. Soc., 1993, 115, 11612;
15. (k) E. Vedejs, S. C. Fields, and M. R. Schrimpf, J. Org. Chem., 1995, 60, 3028.
16. (a) N. Farfán and R. Contreras, Heterocycles, 1985, 23, 2989;
17. (b) T. Mancilla, R. Contreras, and B. Wrackmeyer, J. Organomet. Chem., 1986, 307, 1;
18. (c) N. Farfán, T. Mancilla, D. Castillo, G. Uribe, L. Carrillo, P. Joseph-Nathan, and R. Contreras, J. Organomet. Chem., 1990, 381, 1;
19. (d) R. Contreras, C. Garcia, and T. Mancilla, J. Organomet. Chem., 1983, 246, 213.
20. (a) M. S. Korobov, L. E. Nivorozhkin, L. E. Konstantinovski, and V. I . Minkin, J. Chem.Soc., Chem. Commun., 1982, 169;
21. (b) S. Ingemann, J. C. Kleingeld, and N. M. M. Nibbering, J. Chem.Soc., Chem. Commun., 1982, 1008.
22. J. Chandrasekharan, P. V. Ramachandran, and H. C. Brown, J. Org. Chem., 1985, 50, 5446.
23. H. Nöth and B. Wrackmeyer, NMR: Basic Princ. Prog., 1978, 14.
24. The authors have deposited atomic coordinates for these structures with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
25. (a) S. J. Retting and J. Trotter, Can. J. Chem., 1975, 53, 1393;
26. (b) N. Farfán, P. Joseph, L. M. Chiquete, and R. Contreras, J. Organomet. Chem., 1988, 348, 149.
27. 2-(3-Methyl-buta-1(E),3-dienyl)benzo[1,3,2]dioxaborole undergoes a stable ate complexe upon treatment with caesium fluoride. Functionalized allylborates cycloadducts derived from an endo transition state are exclusively obtained when this ate complexe is reacted with activated dienophiles: L. Gamier, B. Plunian, J. Mortier, and M. Vaultier, Tetrahedron Lett., 1996, 37, 6699.
28. H. C. Brown and G. Zweifel, J. Am. Chem. Soc., 1966, 88, 1433.
29. G. W. Kabalka, R. J. Newton Jr., and J. Jacobus, J. Org. Chem., 1978, 43, 1567.
30. A. Mosandl, M. Gessner, C. Gunther, W. Deger, and G. Singer, J. High Resol. Chrom., Chrom. Commun., 1987, 10, 67.