Stereospecific 1,4-addition of organolithium reagents to unprotected 1-and 2-naphthalenecarboxylic acids. A facile route to 1,1,2- and -1,2,2-trisubstituted 1,2-dihydronaphthalenes

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5206-5207

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

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001503057     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960934z     Document Type: Article

References (30)

1. Wakefield, B. J. The Chemistry of Organolithium Compounds; Pergamon Press: New York, 1974.
2. (a) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Tetrahedron Organic Chemistry Series; Pergamon Press: Oxford, 1992; Vol. 9.
3. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771.
4. Review: Hunt, D. A. Org. Prep. Proced. Int. 1989, 21, 705.
5. Seebach, D.; Ertas, M.; Schweizer, W. B. Helv. Chim. Acta 1985, 68, 264.
6. Occasional reports of conjugate addition reactions of organolithium reagents to unsaturated sec-butyl and tert-butyl esters have also appeared: (a) Munch-Peterson, J. J. Org. Chem. 1957, 22, 170. (b) Munch-Peterson, J. Org. Synth. 1961, 41, 60. (c) Cooke, M. P., Jr. Org. Synth. 1984, 49, 1144.
7. Occasional reports of conjugate addition reactions of organolithium reagents to unsaturated sec-butyl and tert-butyl esters have also appeared: (a) Munch-Peterson, J. J. Org. Chem. 1957, 22, 170. (b) Munch-Peterson, J. Org. Synth. 1961, 41, 60. (c) Cooke, M. P., Jr. Org. Synth. 1984, 49, 1144.
8. Occasional reports of conjugate addition reactions of organolithium reagents to unsaturated sec-butyl and tert-butyl esters have also appeared: (a) Munch-Peterson, J. J. Org. Chem. 1957, 22, 170. (b) Munch-Peterson, J. Org. Synth. 1961, 41, 60. (c) Cooke, M. P., Jr. Org. Synth. 1984, 49, 1144.
9. First report on the Michael-type reactivity of α,β-unsaturated amides: (a) Gilbert, G.; Aycock, B. F. J. Org. Chem. 1957, 22, 1013. Conjugate addition of organolithium reagents to unsaturated secondary and tertiary thioamides: (b) Tamaru, Y.; Kagotani, M.; Furukawa, Y.; Amino, Y.; Yoshida, Z. Tetrahedron Lett. 1981, 22, 3413.
10. First report on the Michael-type reactivity of α,β-unsaturated amides: (a) Gilbert, G.; Aycock, B. F. J. Org. Chem. 1957, 22, 1013. Conjugate addition of organolithium reagents to unsaturated secondary and tertiary thioamides: (b) Tamaru, Y.; Kagotani, M.; Furukawa, Y.; Amino, Y.; Yoshida, Z. Tetrahedron Lett. 1981, 22, 3413.
11. Cooke, M. P., Jr. J. Org. Chem. 1986, 51, 1637.
12. (a) Klein, J.; Turkel, R. M. J. Am. Chem. Soc. 1969, 91, 6186.
13. (b) Klein, J.; Zitrin, S. J. Org. Chem. 1970, 35, 666.
14. (c) Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Ishihara, Y.; Maruyama, K. J. Org. Chem. 1982, 47, 119.
15. (a) Mortier, J.; Moyroud, J.; Bennetau, B.; Cain, P. A. J. Org. Chem. 1994, 59, 4042.
16. (b) Moyroud, J.; Guesnet, J. L.; Bennetau, B.; Mortier, J. Tetrahedron Lett. 1995, 36, 881.
17. (c) Bennetau, B.; Mortier, J.; Moyroud, J.; Guesnet, J. L. J. Chem. Soc., Perkin Trans. 1 1995, 1265.
18. (d) Moyroud, J.; Guesnet, J.-L.; Bennetau, B.; Mortier, J. Bull. Soc. Chim. Fr. 1996, 133, 133.
19. (e) Moyroud, J.; Chêne, A.; Guesnet, J.-L.; Mortier, J. Heterocycles 1996, 43, 221.
20. The functionalization of chiral 1- and 2-naphthyloxazolines has become a prominent route by which many important chiral organic compounds are accessed: Meyers, A. I.; Lutomski, K. A.; Laucher, D. Tetrahedron 1988, 44, 3107 and references cited therein.
21. For addition of organolithium to naphthalene and Grignard addition to acylnaphthalenes, ate complexes of boranes, arene-Cr-(CO)3 complexes, 2,6-di-tert-butyl-4-(methoxyphenyl)-1- and -2-naphthalenecarboxylates (BHA esters), see: (a) Tomioka, K.; Shindo, M.; Koga, K. Tetrahedron Lett. 1993, 34, 681. (b) Kündig, E. P.; Ripa, A.; Liu, R.; Bernardinelli, G. J. Org. Chem. 1994, 59, 4773 and references cited therein. (c) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429. Ortho-metalation appears to be the major reaction pathway in the carboxamides when they are in the 1- and the 2-positions of the naphthalene: (d) Mpango, G. B.; Mahalanabis, K. K.; Madhavi, Z.; Snieckus, V. Tetrahedron Lett. 1980, 21, 4823.
22. For addition of organolithium to naphthalene and Grignard addition to acylnaphthalenes, ate complexes of boranes, arene-Cr-(CO)3 complexes, 2,6-di-tert-butyl-4-(methoxyphenyl)-1- and -2-naphthalenecarboxylates (BHA esters), see: (a) Tomioka, K.; Shindo, M.; Koga, K. Tetrahedron Lett. 1993, 34, 681. (b) Kündig, E. P.; Ripa, A.; Liu, R.; Bernardinelli, G. J. Org. Chem. 1994, 59, 4773 and references cited therein. (c) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429. Ortho-metalation appears to be the major reaction pathway in the carboxamides when they are in the 1- and the 2-positions of the naphthalene: (d) Mpango, G. B.; Mahalanabis, K. K.; Madhavi, Z.; Snieckus, V. Tetrahedron Lett. 1980, 21, 4823.
23. For addition of organolithium to naphthalene and Grignard addition to acylnaphthalenes, ate complexes of boranes, arene-Cr-(CO)3 complexes, 2,6-di-tert-butyl-4-(methoxyphenyl)-1- and -2-naphthalenecarboxylates (BHA esters), see: (a) Tomioka, K.; Shindo, M.; Koga, K. Tetrahedron Lett. 1993, 34, 681. (b) Kündig, E. P.; Ripa, A.; Liu, R.; Bernardinelli, G. J. Org. Chem. 1994, 59, 4773 and references cited therein. (c) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429. Ortho-metalation appears to be the major reaction pathway in the carboxamides when they are in the 1- and the 2-positions of the naphthalene: (d) Mpango, G. B.; Mahalanabis, K. K.; Madhavi, Z.; Snieckus, V. Tetrahedron Lett. 1980, 21, 4823.
24. For addition of organolithium to naphthalene and Grignard addition to acylnaphthalenes, ate complexes of boranes, arene-Cr-(CO)3 complexes, 2,6-di-tert-butyl-4-(methoxyphenyl)-1- and -2-naphthalenecarboxylates (BHA esters), see: (a) Tomioka, K.; Shindo, M.; Koga, K. Tetrahedron Lett. 1993, 34, 681. (b) Kündig, E. P.; Ripa, A.; Liu, R.; Bernardinelli, G. J. Org. Chem. 1994, 59, 4773 and references cited therein. (c) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429. Ortho-metalation appears to be the major reaction pathway in the carboxamides when they are in the 1- and the 2-positions of the naphthalene: (d) Mpango, G. B.; Mahalanabis, K. K.; Madhavi, Z.; Snieckus, V. Tetrahedron Lett. 1980, 21, 4823.
25. 13C NMR and combustion analysis in full agreement with the proposed structures. See the supporting information.
26. 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 Cryatallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
27. The major isomers 4a-c and 6a were obtained pure by fractional recrystallization (heptane/EtOAc).
28. The stereochemical assignent of 4e and 6c was also found to be cis at C1 and C2 via NOE (10%, 5%) while the relative configuration may be assumed to be as drawn (1S*,2S* and 1R*,2R*).
29. Facile additions to naphthalene oxazolines of organolithium reagents derived from LiDBB (lithium 4,4′-di-tert-butylphenyl) have been reported: Rawson, D. J.; Meyers, A. I. Tetrahedron Lett. 1991, 32, 2095 and references cited therein.
30. Traces of 4d,d′ and 6b,b′ could be detected by NMR analysis of the crude reaction mixture.