Stereospecific Synthesis of Optically Active Phenylpropylene Oxides

Journal of Organic Chemistry

Volumn 69, Issue 10, 2004, Pages 3330-3335

  Capriati, Vito ^a   Florio, Saverio ^a   Luisi, Renzo ^a   Nuzzo, Irene ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AROMATIC COMPOUNDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ELECTROPHILES; STEREOSCOPIC LITHIATION; TRAPPING REACTION;

POLYPROPYLENE OXIDES;

PHENYLPROPYLENE OXIDE; PROPYLENE OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 2442515215     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035858w     Document Type: Article

References (53)

1. (a) Besse, P.; Veschambre, H. Tetrahedron 1994, 50, 8885-8927.
2. (b) Bonini, C.; Righi, G. Tetrahedron 2002, 58, 4981-5021.
3. (c) Behrens, C. H.; Katsuki, T. Coord. Chem. Rev. 1995, 140, 189-214.
4. Chung, Y.-M.; Rhee, H.-K. Catal. Lett. 2002, 82, 249-253.
5. (a) A synthesis of enantiomerically pure substituted tetrahydrofurans, promoted by organoselenium reagents, from optically active 1-phenylpropylene oxides has been recently described: Tiecco, M.; Testaferri, L.; Bagnoli, L.; Purgatorio, V.; Temperini, A.; Marini, F.; Santi, C. Tetrahedron: Asymmetry 2004, 15, 405-412.
6. (b) Kamimura, A.; Mitsudera, H.; Matsuura, K.; Omata, Y.; Shirai, M.; Yokoyama, S.; Kakehi, A. Tetrahedron 2002, 58, 2605-2611.
7. (a) Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378-4380.
8. (b) Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5-26.
9. Tian, H.; She, X.; Yu, H.; Shu, L.; Shi, Y. J. Org. Chem. 2002, 67, 2435-2446.
10. (a) Denmark, S. E.; Wu, Z. J. Org. Chem. 1998, 63, 2810-2811.
11. (b) Denmark, S. E.; Wu, Z. Synlett 1999, 847-859.
12. Page, P. C. B.; Rassias, G. A.; Barros, D.; Ardakani, A.; Buckley, B.; Bethell, D.; Smith, T. A. D.; Slawin, A. M. Z. J. Org. Chem. 2001, 66, 6926-6931.
13. Hansen, R. M. Chem. Rev. 1991, 91, 437-475.
14. Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237-6240.
15. Adam, W.; Prikhodovski, S.; Roschmann, K. J.; Saha-Möller C. R. Tetrahedron: Asymmetry 2001, 12, 2677-2681.
16. For some recent reviews on oxiranyl anions, see: (a) Satoh, T. Chem. Rev. 1996, 96, 3303-3325.
17. (b) Mori, Y. Rev. Heteroatom Chem. 1997, 17, 183-211.
18. (c) Hodgson, D. M.; Gras, E. Synthesis 2002, 12, 1625-1642.
19. (d) Florio, S., Ed. Oxiranyl and aziridinyl anions as reactive intermediates in synthetic organic chemistry. Tetrahedron 2003, 59, 9683-9864.
20. (a) Abbotto, A.; Capriati, V.; Degennaro, L.; Florio, S.; Luisi, R.; Pierrot, M.; Salomone, A. J. Org. Chem. 2001, 66, 3049-3058 and references therein.
21. (b) Capriati, V.; Favia, R.; Florio, S.; Luisi, R. ARKIVOC 2003, (xiv), 77-86.
22. (c) Luisi, R.; Capriati, V.; Carlucci, C.; Degennaro, L.; Florio, S. Tetrahedron 2003, 59, 9707-9712.
23. (d) Luisi, R.; Capriati, V.; Degennaro L.; Florio, S. Tetrahedron 2003, 59, 9713-9718.
24. (e) Luisi, R.; Capriati, V.; Degennaro L.; Florio, S. Org. Lett. 2003, 5, 2723-2726.
25. (f) Capriati, V.; Degennaro, L.; Favia, R.; Florio, S.; Luisi, R. Org. Lett. 2002, 4, 1551-1554.
26. (g) Capriati, V.; Florio, S.; Luisi, R.; Salomone, A. Org. Lett. 2002, 4, 2445-2448.
27. Castedo, L.; Castro, J. L.; Riguera, R. Tetrahedron Lett. 1984, 25, 1205-1208.
28. Shu, L.; Shi, Y. J. Org. Chem. 2000, 65, 8807-8810.
29. Foltz, C. M.; Witkop, B. J. Am. Chem. Soc. 1957, 79, 201-205.
30. 3), respectively.
31. (b) Having used up to 3 equiv of s-BuLi and in consideration of the fact that unactivated epoxides can also undergo direct deprotonation (s-BuLi/TMEDA) to give destabilized oxiranyllithiums (Hodson, D. M.; Gras, E. Angew Chem., Int. Ed. 2002, 41, 2376-2378), we also checked enantiomeric purity of an the chiral nonracemic substituted phenylpropylene oxides synthesized, even if the dr would have been sufficient to ascertain the configurational stability of their lithiated precursors.
32. Marié, J.-C.; Courillon, C.; Malacria, M. Synlett 2002, 4, 553-556.
33. (a) Boche, G.; Lohrenz, J. C. W. Chem. Rev. 2001, 101, 697-756.
34. (b) Lohse, P.; Loner, H.; Acklin, P.; Sternfeld, F.; Pfaltz, A. Tetrahedron Lett. 1991, 32, 615-618.
35. (a) Crandall, J. K.; Lin, L.-H. C. J. Am. Chem. Soc. 1967, 89, 4526-4527; (b) 1967, 89, 4527-4528.
36. (a) Crandall, J. K.; Lin, L.-H. C. J. Am. Chem. Soc. 1967, 89, 4526-4527; (b) 1967, 89, 4527-4528.
37. (c) Doris, E.; Dechoux, L.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 7943-7946 and references therein.
38. (d) Hogson, D. M.; Stent, M. A. H.; Wilson, F. X. Synthesis 2002, 1445-1453.
39. (e) An NMR-spectroscopic study on lithiated phenylpropylene oxides is under way and will be reported in due course.
40. The preparation of only a mixture of the optically active trans- and cis-epoxides 3b/3f has been reported till now: Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224-11235.
41. Spectroscopic data of racemic trans-epoxide 3c have been reported in: Yano, K.; Hatta, Y.; Baba, A.; Matsuda, H. Synthesis 1992, 693-696.
42. Molander, G. A.; Mautner, K. Pure Appl. Chem. 1990, 62, 707-712.
43. The convention employed for describing syn and anti diastereomers is as follows: if the main chain is written in an extended (zigzag) conformation, the diastereomer that has the oxiranyl ring and the hydroxy group both projecting either forward (bold bonds) or away from the viewer (dashed bonds) is called syn.
44. CCDC-232045 contains the supplementary crystallographic data for compound (±)-3j. These data can be obtained free of charge at www.ccdc.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK.; Fax: (int) +44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk.
45. Seco, J. M.; Quiñoá, E.; Riguera, R. Chem. Rev. 2004, 104, 17-117.
46. Maruoka, K.; Sato, J.; Yamamoto, H. Tetrahedron 1992, 48, 3749-3762.
47. For a recent review on epoxy ketones as versatile building blocks in organic synthesis, see: Lauret, C. Tetrahedron: Asymmetry 2001, 12, 2359-2383.
48. (a) Taniguchi, M.; Fujii, H.; Oshima, K.; Utimoto, K. Tetrahedron 1995, 51 (3) 679-686.
49. (b) Hojo, M.; Fujii, A.; Murakami, C.; Aihara, H.; Hosomi, A. Tetrahedron Lett. 1995, 36, 571-574.
50. (c) Yun, J. M.; Sim, T. B.; Hahm, H. S.; Lee, W. K. J. Org. Chem. 2003, 68, 7675-7680.
51. α-C=O bond. To introduce electron correlation in the computation of the energetics, the two local minimum-energy conformers found (corresponding just to those represented in Scheme 4 with the phenyl ring perpendicular to the C=O moiety) were subjected to single-point calculations using the density functional theory (DFT) at the B3LY/6-31 + G*/PM3 level of theory: the conformer having the oxiranyl oxygen anti to the C=O group, predicted to be the more reactive one, also resulted to be the more stable one of about 3.7 kca1/mol.
52. (a) Lodge, E. P.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 109, 3353-3361.
53. (b) Gawley, R. E.; Aubè J. In Principle of Asymmetric Synthesis; Baldwin, J. E., FRS, Magnus P. D., Eds.; Elsevier: New York, 1996.