Boron aldol additions with erythrulose derivatives: Dependence of stereoselectivity on the type of protecting group

Tetrahedron Letters

Volumn 40, Issue 37, 1999, Pages 6845-6848

  Carda, Miguel ^a   Falomir, Eva ^a   Murga, Juan ^a   Castillo, Encarnación ^a   González, Florenci ^a   Marco, J Alberto ^b  

^a UNIVERSITAT JAUME I   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BENZYL DERIVATIVE; BORON DERIVATIVE; CHLORINE DERIVATIVE; KETOSE;

ARTICLE; CHEMICAL REACTION KINETICS; REACTION ANALYSIS; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033543725     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01380-5     Document Type: Article

References (39)

1. (a) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1-115.
2. (b) Mukaiyama, T. Org. React. 1982, 28, 203-331.
3. (c) Evans, D. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, pp. 1-110.
4. (d) Heathcock, C. H. ibid., pp. 111-212.
5. (e) Heathcock, C. H. Aldrichimica Acta 1990, 23, 99-111.
6. (f) Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Winterfeldt, E., Eds.; Pergamon Press: Oxford, 1993; Vol. 2.
7. (g) Mekelburger, H. B.; Wilcox, C. S. ibid., pp. 99-131.
8. (h) Heathcock, C. H. ibid., pp. 133-179 and 181-238.
9. (i) Kim, B. M.; Williams, S. F.; Masamune, S. ibid., pp. 239-275.
10. (j) Rathke, M. W.; Weipert, P. ibid., pp. 277-299.
11. (k) Paterson, I. ibid., pp. 301-319.
12. (l) Franklin, A. S.; Paterson, I. Contemp. Org. Synth. 1994, 1, 317-338.
13. (m) Braun, M. In HoubenWeyl's Methods of Organic Chemistry, Stereoselective Synthesis; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann E., Eds.; Georg Thieme Verlag: Stuttgart, 1996; Vol. 3, pp. 1603-1666, 1713-1735.
14. (a) Recent Progress in the Chemical Synthesis of Antibiotics; Lukacs, G.; Ohno, M., Eds.; Springer: Berlin, 1990.
15. (b) Tatsuta, K. ibid., pp. 1-38.
16. (c) Blizzard, T.; Fisher, M.; Mrozik, H.; Shih, T. ibid, pp. 65-102.
17. (d) Isobe, M. ibid., pp. 103-134.
18. (e) Beau, J.-M. ibid., pp. 135-182.
19. (f) Yonemitsu, O.; Horita, K. ibid., pp. 447-466.
20. (g) Norcross, R. D.; Paterson, I. Chem. Rev. 1995, 95, 2041-2114.
21. Marco, J. A.; Carda, M.; Falomir, E.; Palomo, C.; Oiarbide, M.; Ortiz, J. A.; Linden, A. Tetrahedron Lett. 1999, 40, 1065-1068.
22. 5).
23. Marco, J. A.; Carda, M.; González, F.; Rodríguez, S.; Murga, J. Liebigs Ann. Chem. 1996, 1801-1810.
24. (a) Mukaiyama, T. Aldrichimica Acta 1996, 29, 59-76.
25. (b) Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866-868.
26. 2NEt (see: Rossi, T.; Marchioro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653-1661). The aldols formed were, however, identical to those obtained with dicyclohexylboron chloride. These results will be published in due course.
27. (a) Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499-2506.
28. (b) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. Engl. 1998, 37, 180-182, and references cited therein.
29. Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1-200.
30. Brown, H. C.; Ganesan, K.; Dhar, R. K. J. Org. Chem. 1993, 58, 147-153.
31. 3 Chemical yields: 4a (87%), 4b (86%), 4c (83%), 4d (86%), 4e (89%), 9a (87%), 9b (86%), 9c (83%), 9d (86%).
32. Paterson, I.; Channon, J. A. Tetrahedron Lett. 1992, 33, 797-800.
33. The computational calculations will be published in due course.
34. (a) Paterson, I.; Wallace, D. J.; Velázquez, S. M. Tetrahedron Lett. 1994, 35, 9083-9086.
35. (b) Paterson, I.; Wallace, D. J.; Cowden, C. J. Synthesis 1998, 639-652.
36. Whether or not this behaviour in boron aldol additions constitutes a general feature of alkoxy ketones is being currently investigated within our group.
37. All experimental details about the synthetic procedures, chemical correlations, etc. are part of the Ph.D. Thesis of E.F. (University of Castellón, 1998). Complete theoretical and experimental data will be reported in due course.
38. Rychnovsky, S. D.; Rogers, B. N.; Richardson, T. I. Acc. Chem. Res. 1998, 31, 9-17.
39. 4 reduction of aldols has some precedent: Paterson, I.; Wallace, D. J. Tetrahedron Lett. 1994, 35, 9087-9090. To the best of our knowledge, however, this is the first example of an anti reduction taking place in situ.