Structural feature relevance of the chiral alkyl residue in the addition alkanesulfenic acids/enynes. Synthesis and diels-alder reactivity of enantiopure (E)-3-[(1S-exo)-2-bornylsulfinyl]-1methoxybuta-1,3-dienes

Journal of Organic Chemistry

Volumn 64, Issue 6, 1999, Pages 2114-2118

  Aversa, Maria C ^a   Barattucci, Anna ^a   Bonaccorsi, Paola ^a   Giannetto, Placido ^a   Nicolò, Francesco ^a  

^a UNIVERSITY OF MESSINA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 BORNYLSULFINYL 1 METHOXYBUTA 1,3 DIENE; ALKADIENE; UNCLASSIFIED DRUG;

CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; NOTE; ORGANIC CHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033583276     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981262a     Document Type: Note

References (24)

1. (a) Arce, E.; Carreño, M. C.; Cid, M. B.; García Ruano, J. L. J. Org. Chem. 1994, 59, 3421-3426.
2. (b) Gosselin, P.; Bonfand, E.; Hayes, P.; Retoux, R.; Maignan, C. Tetrahedron: Asymmetry 1994, 5, 781-784.
3. (c) Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P. Tetrahedron: Asymmetry 1997, 8, 1339-1367.
4. (d) Carreño, M. C.; Cid, M. B.; García Ruano, J. L.; Santos, M. Tetrahedron: Asymmetry 1997, 8, 2093-2097.
5. (e) Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P.; Jones, D. N. J. Org. Chem. 1997, 62, 4376-4384.
6. Aceña, J. L.; Arjona, O.; Fernández de la Pradilla, R.; Plumet, J.; Vise, A. J. Org. Chem. 1994, 59, 6419-6424 and references therein.
7. Rollin, P. Tetrahedron Lett. 1986, 27, 4169-4170.
8. A previously reported procedure (Blanco, J. M.; Caamaño, O.; Eirin, A.; Fernández, F.; Medina, L. Synthesis 1990, 584-586) for the synthesis of thiol 5, from commercial borneol 3, was performed in three steps and 59% total yield.
9. Brandsma, L. Preparative Acetylenic Chemistry; Elsevier: Amsterdam, 1971.
10. Fernández de la Pradilla, R.; Martínez, M. V.; Montera, C.; Viso, A. Tetrahedron Lett. 1997, 38, 7773-7776.
11. Davis, F. A.; Jenkins, L. A.; Billmers, R. L. J. Org. Chem. 1986, 51, 1033-1040.
12. Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Bruno, G.; Giannetto, P.; Nicolò, F. J. Chem. Soc., Perkin Trans. 2 1997, 273-277.
13. Nakamura, N. J. Am. Chem. Soc. 1983, 105, 7172-7173.
14. Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P.; Panzalorto, M.; Rizzo, S. Tetrahedron: Asymmetry 1998, 9, 1577-1587.
15. Rogers, D. Acta Crystallogr. 1981, A37, 734-741. Flack, H. D. Acta Cryst. 1983, A39, 876-881.
16. Rogers, D. Acta Crystallogr. 1981, A37, 734-741. Flack, H. D. Acta Cryst. 1983, A39, 876-881.
17. Molecular Modeling Program: CS Chem3D Pro, version 3.5. Force field: MM2.
18. (a) Durst, T.; Tin, K. C.; De Reinach-Hirtzbach, F.; Decesare, J. M.; Ryan, M. D. Can. J. Chem. 1979, 57, 258-266.
19. (b) Clark, C.; Hermans, P.; Meth-Cohn, O.; Moore, C.; Taljaard, H. C.; van Vuuren, G. J. Chem. Soc., Chem. Commun. 1986, 1378-1380.
20. (c) Jackson, R. F. W.; Standen, S. P.; Clegg, W.; McCamley, A. Tetrahedron Lett. 1992, 33, 6197-6200.
21. (d) Bueno, A. B.; Carreño, M. C.; García Ruano, J. L. Tetrahedron Lett. 1993, 34, 5007-5010.
22. R), although they have different designations according to the CIP system.
23. R (6.45 and 3.43 ppm).
24. Pfenninger, A. Synthesis 1986, 89-115.