Unified approach towards medium ring allylic ethers. Stereoselective synthesis of 2,10-dialkylated (E)-oxacyclodec-3-enes by palladium catalyzed cyclization

Tetrahedron Letters

Volumn 39, Issue 39, 1998, Pages 7085-7088

  Hoffmann, H M R ^a   Pohlmann, J ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

Mechanisms; Oxygen heterocycles; Stereocontrol

Indexed keywords

PALLADIUM;

ALKYLATION; ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; EPOXIDATION; HYDROGENATION; NONHUMAN; SIALYLATION; X RAY DIFFRACTION;

EID: 0032563905     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01506-8     Document Type: Article

References (23)

1. 1 Brandes, A.; Hoffmann, H. M. R. Tetrahedron 1995, 51, 145.
2. 2 Hoffmann, H. M. R.; Brandes, A. Tetrahedron 1995, 51, 155.
3. 3 Brandes, A.; Eggert, U.; Hoffmann, H. M. R. Synlett. 1994, 745.
4. 4 For accounts of the extensive primary literature and Pd-mediated allylic alkylations (Trost-Tsuji reactions) see: a) Tsuji, J. Palladium Reagents and Catalysts. Innovations in Organic Synthesis, Wiley, Chichester, 1997;
5. b) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422;
6. c) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089-1122;
7. d) Godleski, S. A. in Comprehensive Organic Synthesis, Vol. 4, Eds.: Trost, B. M.; Fleming, I.; Semmelhack, M. F. Pergamon, Oxford, 1991, pp. 585-661;
8. e) Trost, B. M. Angew. Chem. 1989, 101, 1199-1219; Angew. Chem. Int. Ed. Engl. 1989, 28, 1173-1192.
9. e) Trost, B. M. Angew. Chem. 1989, 101, 1199-1219; Angew. Chem. Int. Ed. Engl. 1989, 28, 1173-1192.
10. 5 Pohlmann, J.; Sabater, C.; Hoffmann, H. M. R. Angew. Chem. 1998, 110, 656; Angew. Chem. Int. Ed. Engl. 1998, 37, 633.
11. 5 Pohlmann, J.; Sabater, C.; Hoffmann, H. M. R. Angew. Chem. 1998, 110, 656; Angew. Chem. Int. Ed. Engl. 1998, 37, 633.
12. 6 See ref. 2, footnote 11.
13. 3), 25.34 (+, C8), 27.26 (+, C7), 36.15 (+, C5), 65.69 (-, C9), 75.37, 78.09 (-, C2, C10), 91.23 (+, C6), 128.64, 131.21, 131.40 (-, arom. CH), 132.04 (-, C3), 134.48, 136.01 (-, arom. CH), 136.01 (+, arom. C), 137.37 (-, C4), 137.43 (+, arom. C).
14. 8 Wartchow, R.; Pohlmann, J.; Hoffmann, H. M. R., unpublished.
15. 9 For alcohols and alkoxides as nucleophiles in allylic alkylation see Cuiper, A. D.; Kellogg, R. M.; Feringa, B. M. J. Chem. Soc., Chem. Commun. 1998, 655; Davis, A. P.; Dorgan, B. J.; Mageean, E. R. J. Chem. Soc., Chem. Commun. 1993, 492; Larock, R. C.; Lee, N. H. J. Org. Chem. 1991, 56, 6253; Lakhmiri, R.; Lhoste, P.; Sinou, D. Synth. Commun. 1990, 20, 1551; Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2927, 2931; Guibe, F.; Saint M'Leux, Y. Tetrahedron Lett. 1981, 22, 3591.
16. 9 For alcohols and alkoxides as nucleophiles in allylic alkylation see Cuiper, A. D.; Kellogg, R. M.; Feringa, B. M. J. Chem. Soc., Chem. Commun. 1998, 655; Davis, A. P.; Dorgan, B. J.; Mageean, E. R. J. Chem. Soc., Chem. Commun. 1993, 492; Larock, R. C.; Lee, N. H. J. Org. Chem. 1991, 56, 6253; Lakhmiri, R.; Lhoste, P.; Sinou, D. Synth. Commun. 1990, 20, 1551; Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2927, 2931; Guibe, F.; Saint M'Leux, Y. Tetrahedron Lett. 1981, 22, 3591.
17. 9 For alcohols and alkoxides as nucleophiles in allylic alkylation see Cuiper, A. D.; Kellogg, R. M.; Feringa, B. M. J. Chem. Soc., Chem. Commun. 1998, 655; Davis, A. P.; Dorgan, B. J.; Mageean, E. R. J. Chem. Soc., Chem. Commun. 1993, 492; Larock, R. C.; Lee, N. H. J. Org. Chem. 1991, 56, 6253; Lakhmiri, R.; Lhoste, P.; Sinou, D. Synth. Commun. 1990, 20, 1551; Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2927, 2931; Guibe, F.; Saint M'Leux, Y. Tetrahedron Lett. 1981, 22, 3591.
18. 9 For alcohols and alkoxides as nucleophiles in allylic alkylation see Cuiper, A. D.; Kellogg, R. M.; Feringa, B. M. J. Chem. Soc., Chem. Commun. 1998, 655; Davis, A. P.; Dorgan, B. J.; Mageean, E. R. J. Chem. Soc., Chem. Commun. 1993, 492; Larock, R. C.; Lee, N. H. J. Org. Chem. 1991, 56, 6253; Lakhmiri, R.; Lhoste, P.; Sinou, D. Synth. Commun. 1990, 20, 1551; Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2927, 2931; Guibe, F.; Saint M'Leux, Y. Tetrahedron Lett. 1981, 22, 3591.
19. 9 For alcohols and alkoxides as nucleophiles in allylic alkylation see Cuiper, A. D.; Kellogg, R. M.; Feringa, B. M. J. Chem. Soc., Chem. Commun. 1998, 655; Davis, A. P.; Dorgan, B. J.; Mageean, E. R. J. Chem. Soc., Chem. Commun. 1993, 492; Larock, R. C.; Lee, N. H. J. Org. Chem. 1991, 56, 6253; Lakhmiri, R.; Lhoste, P.; Sinou, D. Synth. Commun. 1990, 20, 1551; Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2927, 2931; Guibe, F.; Saint M'Leux, Y. Tetrahedron Lett. 1981, 22, 3591.
20. 9 For alcohols and alkoxides as nucleophiles in allylic alkylation see Cuiper, A. D.; Kellogg, R. M.; Feringa, B. M. J. Chem. Soc., Chem. Commun. 1998, 655; Davis, A. P.; Dorgan, B. J.; Mageean, E. R. J. Chem. Soc., Chem. Commun. 1993, 492; Larock, R. C.; Lee, N. H. J. Org. Chem. 1991, 56, 6253; Lakhmiri, R.; Lhoste, P.; Sinou, D. Synth. Commun. 1990, 20, 1551; Trost, B. M.; Tenaglia, A. Tetrahedron Lett. 1988, 29, 2927, 2931; Guibe, F.; Saint M'Leux, Y. Tetrahedron Lett. 1981, 22, 3591.
21. 10 Ion pair return was discovered and established in reactions of free, uncomplexed allylic cations. For the work of Winstein and Ingold see, e.g. March, J. Adv. Org. Chem., Wiley 1992, 327-330.
22. a 13.3) as leaving group: Nilsson, Y. I. M.; Andersson, P. G.; Bäckvall, J. E. J. Am. Chem. Soc. 1993, 115, 6609.
23. 12 For simple 2,n-dialkylated oxacycloalkanes (ring size n) the cis arrangement of alkyl groups is usually favoured thermodynamically, as in 2,6-cis-diequatorial tetrahydropyrans. The 2,n-trans arrangement, as observed here for n = 8 and n = 9 is usually contrathermodynamic.