Chiral phosphinooxazolines with a Bi- or tricyclic oxazoline moiety - Applications in Pd-catalyzed allylic alkylations

Tetrahedron Letters

Volumn 39, Issue 32, 1998, Pages 5727-5730

  Wiese, Burkhard ^a   Helmchen, Günter ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLINE DERIVATIVE;

ALKYLATION; ARTICLE; CHIRALITY; DRUG SYNTHESIS; GERMANY;

EID: 0032490952     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01173-3     Document Type: Article

References (34)

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18. 6. S. Kudis, G. Helmchen, submitted; cf. also ref. 8.
19. 7. Excellent results for allylic substitutions with 1,3-dimethylallyl methyl carbonate were reported by the Trost group: (a) Trost, B. M.; Radinov, R. J. Am. Chem. Soc. 1997, 119, 5962-5963.
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24. 10. Peer, M.; de Jong, J. C.; Kiefer, M.; Langer, T.; Rieck, H.; Schell, H.; Sennhenn, P.; Sprinz, J.; Steinhagen, H.; Wiese, B.; Helmchen, G. Tetrahedron 1996, 52, 7547-7583.
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27. 2 (88 % yield, diastereoselectivity >95:5) according to a general method of J. Ipaktschi (Chem. Ber. 1984, 117, 856-858); exo-3-hydroxy-2-bornanone was prepared from (1R)-2,3-bornandione by reduction with L-Selectride according to an unpublished procedure kindly communicated by Prof. Y. Langlois, Paris.
28. 2 (88 % yield, diastereoselectivity >95:5) according to a general method of J. Ipaktschi (Chem. Ber. 1984, 117, 856-858); exo-3-hydroxy-2-bornanone was prepared from (1R)-2,3-bornandione by reduction with L-Selectride according to an unpublished procedure kindly communicated by Prof. Y. Langlois, Paris.
29. 13. Both pure enantiomers of cis-1-amino-2-indanol are commercially available (Strem Chemicals, Aldrich).
30. 14. The diol 4 was purchased from Fluka.
31. 15. Senanayake, C. H.; Larsen, R. D.; DiMichele, L. M.; Liu, J.; Toma, P. H.; Ball, R. G.; Verhoeven, T. R.; Reider, P. J. Tetrahedron: Asymmetry 1996, 7, 1501-1506.
32. 16. This statement may appear paradoxical. However, one must bear in mind that the first step in the catalytic cycle, oxidative addition, is fast compared to the second step, nucleophilic substitution. As a consequence, steric strain gives rise to increase of the energy content of the π-allyl complex and, therefore, reduction of the activation energy because interactions between the allylic moiety and the ligand are lower in the transition state than in the ground state.
33. 17. Kiefer, M. Dissertation, Universität Heidelberg, 1995.
34. 18. Wiese, B. Dissertation, Universität Heidelberg, 1997.