Multigram synthesis of diastereomerically pure tetrahydrofuran-diols

Synthesis

Volumn , Issue 17, 2007, Pages 2751-2754

  Göhler, Sabrina ^a   Roth, Stefanie ^a   Cheng, Huan ^a   Göksel, Hülya ^a   Rupp, Alexander ^a   Haustedt, Lars O ^b   Stark, Christian B W ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b ANALYTICON DISCOVERY GMBH   (Germany)

Author keywords

Cyclization; Diastereoselectivity; Heterocycle; Oxidation; Ruthenium

Indexed keywords

DIASTEREOMERIC RATIO; DIASTEREOSELECTIVITY; TETRAHYDROFURAN-DIOLS;

CYCLIZATION; MOISTURE; OXIDATION; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ALCOHOLS;

2 HYDROXY 2 [5 (1 HYDROXY 1 METHYLETHYL) 2 METHYLTETRAHYDROFURAN 2 YL]ETHYL BENZOATE; 2 HYDROXY 2 [5 (1 HYDROXYPROPYL)TETRAHYDROFURAN 2 YL]ETHYLBENZOATE; 4 (TERT BUTYLDIPHENYLSILOXY) 1 [5 [4 (TERT BUTYLDIPHENYLSILOXY) 1 HYDROXYBUTYL]TETRAHDYROFURAN 2 YL]BUTAN 1 OL; ALKADIENE; BENZOIC ACID DERIVATIVE; BUTANOL; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL PROCEDURES; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; OXIDATION; SYNTHESIS;

EID: 34548702643     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983797     Document Type: Article

References (34)

1. 4 (see also refs. 5 and 6): (a) Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
2. (b) Albarella, L.; Musumeci, D.; Sica, D. Eur. J. Org. Chem. 2001, 997.
3. (c) Piccialli, V.; Cavallo, N. Tetrahedron Lett. 2001, 42, 4695.
4. (d) Friedel, M.; Golz, G.; Mayer, P.; Lindel, T. Tetrahedron Lett. 2005, 46, 1623.
5. 4: (e) Klein, E.; Rojahn, W. Tetrahedron 1965, 21, 2353.
6. (f) Walba, D. M.; Wand, M. D.; Wilkes, M. C. J. Am. Chem. Soc. 1979, 101, 4396.
7. (g) Baldwin, J. E.; Crossley, M. J.; Lehtonen, E.-M. M. J. Chem. Soc., Chem. Commun. 1979, 918.
8. (h) Brown, R. C. D.; Keily, J. F. Angew. Chem. Int. Ed. 2001, 40, 4496;
9. Angew. Chem. 2001, 113, 4628.
10. 4: (i) de Champdoré, M.; Lasalvia, M.; Piccialli, V. Tetrahedron Lett. 1998, 39, 9781.
11. (j) Donohoe, T. J.; Butterworth, S. Angew. Chem. Int. Ed. 2003, 42, 948;
12. Angew. Chem. 2003, 115, 978.
13. For a review on the mechanistically related oxidative cyclization of bishomoallylic alcohols, see: Hartung, J.; Greb, M. J. Organomet. Chem. 2002, 661, 67.
14. Oxidation in Organic Chemistry, ACS Monograph Series No. 186; Hudlicky, M., Ed.; American Chemical Society: Washington DC, 1990.
15. (a) Kocieński, P. J.; Brown, R. C. D.; Pommier, A.; Procter, M.; Schmidt, B. J. Chem. Soc., Perkin Trans. 1 1998, 9.
16. (b) Cecil, A. R. L.; Brown, R. C. D. Org. Lett. 2002, 4, 3715.
17. (c) Lygo, B.; Slack, D.; Wilson, C. Tetrahedron Lett. 2005, 46, 6629.
18. (d) Göksel, H.; Stark, C. B. W. Org. Lett. 2006, 8, 3433.
19. (a) Roth, S.; Göhler, S.; Cheng, H.; Stark, C. B. W. Eur. J. Org. Chem. 2005, 4109.
20. (b) Göhler, S.; Stark, C. B. W. Org. Biomol. Chem. 2007, 5, 1605.
21. Roth, S.; Stark, C. B. W. Angew. Chem. Int. Ed. 2006, 45, 6218;
22. Angew. Chem. 2006, 118, 6364.
23. For details see ref. 4d; cf. also: Neogi, P.; Doundoulakis, T.; Yazbak, A.; Sinha, S. C.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 11279.
24. 4-catalyzed oxidations, see: Plietker, B. Synthesis 2005, 2453.
25. Zhong, Y.-L.; Shing, T. K. M. J. Org. Chem. 1997, 62, 2622; see also ref. 5 and 6.
26. Enzyme Catalysis in Organic Synthesis, 2nd ed.; Drauz, K.; Waldmann, H., Eds.; Wiley-VCH: Weinheim, 2002.
27. For enzyme catalyzed esterifications of tetrahydrofurandiols, see ref. 4d; see also: (a) Naemura, K.; Fukada, R.; Takahashi, N.; Konishi, M.; Hirose, Y. Tetrahedron: Asymmetry 1993, 4, 911.
28. (b) Hegemann, K.; Schimanski, H.; Höweler, U.; Haufe, G. Tetrahedron Lett. 2003, 44, 2225.
29. (c) Hegemann, K.; Fröhlich, R.; Haufe, G. Eur. J. Org. Chem. 2004, 2181.
30. Cf. also: (d) Estermann, H.; Prasad, K.; Shapiro, M.; Repic, O.; Hardtmann, G. E.; Bolsterli, J. J.; Walkinshaw, M. D. Tetrahedron Lett. 1990, 31, 445.
31. Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191.
32. McDonald, F. E.; Schultz, C. C. Tetrahedron 1997, 53, 16435.
33. (a) Moore, J. A.; Kelly, J. E. Macromolecules 1978, 11, 568.
34. (b) Nakazaki, M.; Naemura, K.; Makimura, M.; Matsuda, A.; Kawano, T.; Ohta, Y. J. Org. Chem. 1982, 47, 2429.