Development of an asymmetric palladium-catalysed elimination

Tetrahedron Asymmetry

Volumn 7, Issue 9, 1996, Pages 2467-2470

  Koroleva, Elise B ^a   Andersson, Pher G ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030248677     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00308-4     Document Type: Article

References (13)

1. 1. Bäckvall, J. E.; Andersson, P. G.; Stone, G. B.; Gogoll, A. J. Org. Chem., 1991, 56, 2988.
2. 2. (a) Bäckvall, J. E.; Andersson, P. G.; Vågberg, J. O. Tetrahedron Lett. 1989, 30, 137.
3. (b) Bäckvall, J. E.; Granberg, K. L.; Andersson, P. G.; Gatti, R.; Gogoll, A. J. Org. Chem. 1993, 58, 5445.
4. (c) Bäckvall, J. E.; Andersson, P. G. J. Am. Chem. Soc. 1990, 112, 3683.
5. (d) Bäckvall, J. E.; Andersson, P. G. J. Am. Chem. Soc. 1992, 114, 6374.
6. 3. For an asymmetric elimination leading to exo-cyclic dienes see: Hayashi, T.; Kishi, K.; Uozumi Y. Tetrahedron : Asymmetry 1991, 2, 195.
7. 4. Prepared in two steps from (-)-carvone via reduction and alkylation with methyl chloroformiate. For the diastereoselective reduction of (-)-carvone see: Ireland, R. E.; Maienfisch, P. J. Org. Chem. 1988, 53, 640.
8. 2O).
9. 6. (a) Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518.
10. (b) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Tetrahedron: Asymmetry 1991, 2, 569.
11. 7. (-)-Borneol, α-terpineol, (+)-isopinocampheol, (1S)-fenchyl alcohol, (S)-(-)-α-methyl-1 -naphthalene methanol, (+)-isomenthol and (+)-menthol were also studied, but did not lead to any significant diastereoselectivity in the elimination.
12. 8. Weismiller, M. C.; Towson, J. C.; Davis, F. A. Org. Synth., Coll Vol. VIII, 1993, 110
13. 9. Ort, O. Org. Synth. 1987, 65, 203.