1-Methylgeraniol as novel regio- and diastereoselective probe for hydrogen bonding in hydroxy-assisted oxygen-transfer reactions

Liebigs Annales

Volumn , Issue 7, 1997, Pages 1365-1369

  Adam, Waldemar ^a   Mitchel, Catherine M ^a   Paredes, Rodrigo ^b   Smerz, Alexander K ^a   Veloza, L Angela ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b UNIVERSIDAD DEL VALLE   (Colombia)

Author keywords

1 Methylgeraniol; Chemoselectivity; Diastereoselectivity; Epoxidations; Hydrogen bonding; Peroxides

Indexed keywords

EID: 0003727060     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970713     Document Type: Article

References (43)

1. A. H. Hoveyda, D. A. Evans, G. C. Fu, Chem. Rev. 1993, 93, 1307-1370.
2. [2a] W. Adam, A. K. Smerz, Tetrahedron 1995, 51, 13039-13044.
3. [2b] W. Adam, A. K. Smerz, J. Org. Chem. 1996, 61, 3506-3510.
4. W. Adam, R. Kumar, T. I. Reddy, M. Renz, Angew. Chem. 1996, 108, 944-947;
5. Angew. Chem. Int. Ed. Engl. 1996, 55, 880-882.
6. W. Adam, C. M. Mitchell, Angew. Chem. 1996, 108, 578-581;
7. Angew. Chem. Int. Ed. Engl. 1996, 35, 533-535.
8. M. Prein, W. Adam, Angew. Chem. 1996, 108, 519-538;
9. Angew. Chem. Int. Ed. Engl. 1996, 35, 495-513.
10. W. Adam, M. Prein, Acc. Chew. Res. 1996, 29, 275-283.
11. R. Curci, A. Dinoi, M. F. Rubino, Pure Appl. Chem. 1995, 67, 811-822.
12. M. Ferrer, M. Gilbert, F. Sânchez-Baeza, A. Messeguer, Tetrahedron Lett. 1996, 37, 3585-3586.
13. [9a] R. W. Murray, D. Gu, J. Chem. Soc., Perkin Trans. 2 1993, 2203-2207.
14. [9b] A. L. Baumstark, C. J. McCloskey, Tetrahedron Lett. 1987, 28, 3311-3314.
15. [10a] M. Scheller, B. Frei, Helv. Chim. Acta 1992, 75, 69-78.
16. [10b] T. Sato, T. Kikuchi, H. Tsuijita, A. Kaetsu, N. Sootome, K. Nishida, K. Tachibana, E. Murayama, Tetrahedron 1991, 47, 3281-3304.
17. [10c] A. Johns, J. A. Murphy, M. S. Sherburn, Tetrahedron 1989, 45, 7835-7858.
18. M. J. Kamlet, J. L. Abboud, R. W. Taft, J. Am. Chem. Soc. 1977, 99, 6027-6038.
19. R. W. Hoffmann, Chem. Rev. 1989, 89, 1841-1860.
20. R. Mello, M. Fiorentino, O. Sciacovelli, R. Curci, J. Org. Chem. 1988, 53, 3890-3891.
21. [14a] W. Adam, L. Hadjiarapoelou, A. Smerz, Chem. Ber. 1991, 124, 227-232.
22. [14b] D. Yang, Y.-C. Yip, M.-W. Tang, M.-K. Wong, J.-H. Zheng, K.-K. Cheunc, J. Am. Chem. Soc. 1996, 118, 491-492.
23. F. Fringuelli, F. Pizzo, R. Germani, Synlett. 1991, 475-476.
24. [16a] K. B. Sharpless, T. R. Verhoeven, Aldrichimica Acta 1979, 12, 63-74.
25. [16b] A. S. Narula, Tetrahedron Lett. 1983, 24, 5421-5424.
26. [17a] R. Bloch, J. Abecassis, D. Hassan, J. Org. Chem. 1985, 50, 1544-1545.
27. [17b] W. Zhu, W. T. Ford, J. Org. Chem. 1991, 56, 7022-7026.
28. R. Kluge, M. Schulz, S. Liebsch, Tetrahedron 1996, 52, 2957-2976.
29. [19a] W. Adam, A. Griesbeck, E. Staab, Angew. Chem. 1986, 98, 279-280;
30. Angew. Chem. Int. Ed. Engl. 1986, 25, 269-270.
31. [19b] W. Adam, M. Braun, A. Griesbeck, V. Lucchini, E. Staab, B. Will, J. Am. Chem. Soc. 1989, 111, 203-212.
32. [20a] E. D. Mihelich, Tetrahedron Lett. 1979, 4729-4732.
33. [20b] W. Adam, E. Staab, Tetrahedron Lett. 1988, 29, 531-534.
34. [20c] B. E. Rossiter, T. R. Verhoeven, K. B. Sharpless, Tetrahedron Lett. 1979, 4733-4736.
35. E. Höft, H. Kosslick, R. Fricke, H. J. Hamann, J. Prakt. Chem./ Chem. Ztg. 1996, 338, 1-15.
36. P. Behrens, J. Felsche, S. Vetter, G. Schulz-Ekloff, N. I. Jaeger, W. Niemann, J. Chem. Soc., Chem. Commun. 1991, 678-680.
37. W. Adam, A. Corma, I. Reddy, M. Renz, J. Org. Chem., accepted.
38. [24a] R. W. Murray, R. J. Jeyaraman, J. Org. Chem. 1985, 50, 2847-2853.
39. [24b] W. Adam, J. Bialas, L. Hadjiarapoglou, Chem. Ber. 1991, 124, 2377.
40. W. A. Herrmann, J. G. Kuchler, G. Weichselbaumer, E. Herdtweck, P. Kiprof. J. Organomet. Chem. 1989, 572, 351-370.
41. A. Thangaraj, R. Kumar, S. P. Mirajkar, P. Ratnasamy, J. Catal. 1991, 130, 1-8.
42. H. A. Staab, Angew. Chem. 1962, 74, 407-423.
43. D. Yang, M.-K. Wong, Y-C. Yip, J. Org. Chem. 1995, 60, 3887-3889.