Diastereoselective 1,6-additions of lithium amides to naphthyloxazolines. A route to novel δ-amino acid derivatives

Journal of Organic Chemistry

Volumn 61, Issue 17, 1996, Pages 5714-5715

  Shimano, Masanao ^a   Meyers, A I ^a  

^a Immunology and Pathology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; NAPHTHALENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029827163     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960874x     Document Type: Article

References (17)

1. (a) Shimano, M.; Meyers, A. I. J. Am Chem. Soc. 1994, 116, 6437.
2. (b) Shimano, M.; Meyers, A. I. J. Org. Chem. 1995, 60, 7445.
3. A report of 1,4-addition of amide cuprates also briefly described a 1,6-addition of benzylamine to an α,β,γ,δ-dienoate. Yamamoto, Y.; Asao, N.; Uyehara, T. J. Am Chem. Soc. 1992, 114, 5427.
4. There have been several reports of 1,6-substitution reactions of amino functions to the aromatic ring systems; see: (a) Katrizky, A. R.; Laurenzo, K. S. J. Org. Chem. 1986, 51, 5039. (b) Bunce, N. J.; Cater, S. R.; Scaiano, J. C.; Johnston, L. J. J, Org. Chem. 1987, 52, 4214. (c) Makosza, M.; Bialecki, M. J. Org. Chem. 1992, 57, 4784. (d) Seko, S.; Kawamura, N. J. Org. Chem. 1996, 61, 442.
5. There have been several reports of 1,6-substitution reactions of amino functions to the aromatic ring systems; see: (a) Katrizky, A. R.; Laurenzo, K. S. J. Org. Chem. 1986, 51, 5039. (b) Bunce, N. J.; Cater, S. R.; Scaiano, J. C.; Johnston, L. J. J. Org. Chem. 1987, 52, 4214. (c) Makosza, M.; Bialecki, M. J. Org. Chem. 1992, 57, 4784. (d) Seko, S.; Kawamura, N. J. Org. Chem. 1996, 61, 442.
6. There have been several reports of 1,6-substitution reactions of amino functions to the aromatic ring systems; see: (a) Katrizky, A. R.; Laurenzo, K. S. J. Org. Chem. 1986, 51, 5039. (b) Bunce, N. J.; Cater, S. R.; Scaiano, J. C.; Johnston, L. J. J, Org. Chem. 1987, 52, 4214. (c) Makosza, M.; Bialecki, M. J. Org. Chem. 1992, 57, 4784. (d) Seko, S.; Kawamura, N. J. Org. Chem. 1996, 61, 442.
7. There have been several reports of 1,6-substitution reactions of amino functions to the aromatic ring systems; see: (a) Katrizky, A. R.; Laurenzo, K. S. J. Org. Chem. 1986, 51, 5039. (b) Bunce, N. J.; Cater, S. R.; Scaiano, J. C.; Johnston, L. J. J, Org. Chem. 1987, 52, 4214. (c) Makosza, M.; Bialecki, M. J. Org. Chem. 1992, 57, 4784. (d) Seko, S.; Kawamura, N. J. Org. Chem. 1996, 61, 442.
8. Meyers, A. I.; Gant, T. G. J. Org. Chem. 1992, 57, 4225. We recently reported the highly diastereoselective 1,6-addition of lithioallylsilanes to 2-methoxy-1-naphthyloxazolines followed by quenching with alkyl halides. The products thus formed gave >98% trans-1-alkyl- 4-(allylsilyl)-1,4-dihydronaphthalenes.
9. The ratio of the 1,4-adduct to 1,6-adduct in the case of lithium piperidide was 98:2.
10. The lithium amides in Table 1 gave no 1,4-amino adducts in the presence of stoichiometric amounts of HMPA, and only starting oxazoline was recovered.
11. The steric effects of allylic 1,3-strain have been discussed in several reviews: (a) Hoffmann, R. W. Chem. Rev. 1989, 89, 1841. (b) Johnson, F. Chem. Rev. 1968, 68, 375.
12. The steric effects of allylic 1,3-strain have been discussed in several reviews: (a) Hoffmann, R. W. Chem. Rev. 1989, 89, 1841. (b) Johnson, F. Chem. Rev. 1968, 68, 375.
13. It is of interest that use of methyl triflate in place of methyl iodide completely suppressed the formation (< 1%) of the 1,5-tandem methyl product, 4d (Table 1).
14. Laguzza, B. C.; Ganem, B. Tetrahedron Lett. 1981, 22, 1483.
15. No double bond migration in the tetralin ring of 6 was observed during treatment with the Wilkinson catalyst.
16. All new compounds were completely characterized, and these data are included in the supporting information.
17. The author has deposited atomic coordinates for 2b and 2e 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.