Synthesis of enantiomerically pure cyclopropyl boronic esters

Liebigs Annales

Volumn , Issue 11, 1997, Pages 2297-2302

  Luithle, Joachim E A ^a   Pietruszka, Jörg ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

(2R,3R) 1,4 Dimethoxy 1,1,4,4 tetraphenyl 2,3 butanediol; Boronic acids; Boronic esters; Cyclopropanation

Indexed keywords

EID: 0006319534     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719971118     Document Type: Article

References (45)

1. [1a] S. Patai, Z. Rappoport (Eds.), The Chemistry of the Cyclopropyl Group, Wiley, New York, 1987.
2. [1b] H.-U. Reißig, Topics in Current Chemistry, vol. 144 (Ed.: A. de Meijere), Springer Verlag, New York, 1988, 73-135.
3. [1c] J. R. Y. Salaün, Topics in Current Chemistry, vol. 144 (Ed.: A. de Meijere), Springer Verlas, New York, 1988, 1-69.
4. [1d] H. N. C. Wong, M.-Y. Hon, C.-W. Tse, Y. C. Yip, J. Tanko, T. Hudlicky, Chem. Rev. 1989, 89, 165-198.
5. [2a] C. J. Suckling, Angew. Chem. 1988, 100, 555-570;
6. Angew. Chem. Int. Ed. Engl. 1988, 27, 537.
7. [2b] W. H. Gerwick, Chem. Rev. 1993, 93, 1807-1823.
8. [3a] H.-U. Reißig in Stereoselective Synthesis of Organic Compounds/Methods of Organic Chemistry (Houben-Weyl), 4th ed., vol. E21c (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1995, p. 3179-3270.
9. [3b] A. B. Charette, J.-F. Marcoux, Synlett 1995, 1197-1207.
10. [3c] S. E. Denmark, S. P. O' quotation mark, right Conner, J. Org. Chem. 1997, 62, 584-594.
11. [3d] A. H. Hoveyda, D. A. Evans, G. C. Fu, Chem. Rev. 1993, 93, 1307-1370.
12. [3e] T. Ye, M. A. McKervey, Chem. Rev. 1994, 94, 1091-1160.
13. [3f] T. Nagasawa, Y. Handa, Y. Onoguchi, K. Suzuki, Bull. Chem. Soc. Jpn. 1996, 69, 31-39.
14. For a successful method applied for instance in polycyclopropane synthesis, see:[4a] A. B. Charette, H. Juteau, J. Am. Chem. Soc. 1994, 116, 2651-2652.
15. [4b] A. B. Charette, S. Presscott, C. Brocha, J. Org. Chem. 1995, 60, 1081-1083.
16. Applications: [4c] W. McDonald, C. A. Verbicky, C. K. Zercher, J. Org. Chem. 1997, 62, 1215-1222.
17. [4d] A. B. Charette, H. Lebel, J. Am. Chem. Soc. 1996, 118, 10327-10328.
18. [4e] A. G. M. Barrett, K. Kasdorf, J. Am. Chem. Soc. 1996, 118, 11030-11037.
19. [4f] A. G. M. Barrett, D. Hamprecht, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1996, 118, 7863-7864.
20. H.-U. Reißig, Angew. Chem. 1996, 108, 1049-1051;
21. Angew. Chem. Int. Ed. Engl. 1996, 35, 971-973.
22. J. P. Hildebrand, S. P. Marsden, Synlett 1996, 893-894.
23. J. Pietruszka, M. Widenmeyer, Synlett 1997, 977-979.
24. [8a] T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986-4988.
25. [8b] For a review on the chemistry of cyclopropanols, see: D. H. Gibson, C. H. DePuy, Chem. Rev. 1974, 74, 605-623.
26. [9a] A Pelter, K. Smith, H. C. Brown, Borane Reagents, Academic Press, London, 1988.
27. [9b] H. C. Brown, G. W. Kramer, A. B. Levy, M. M. Midland, Organic Synthesis via Boranes, Wiley, New York, 1975.
28. [10a] H. C. Brown, N. G. Bhat, V. Somayaji, Organometallics 1983, 2, 1311-1316.
29. [10b] H. C. Brown, J. B. Campbell, Jr., J. Org. Chem. 1980, 45, 389-395.
30. [10c] H. C. Brown, N. G. Bhat, M. Srebnik, Tetrahedron Lett. 1988, 29, 2631-2634.
31. [10d] M. Srebnik, N. G. Bhat, H. C. Brown, Tetrahedron Lett. 1988, 29, 2635-2638.
32. [11a] P. Fontani, B. Carboni, M. Vaultier, R. Carrie, Tetrahedron Lett. 1989, 30, 4815-4818.
33. [11b] P. Fontani, B. Carboni, M. Vaultier, G. Maas, Synthesis 1991, 605-609.
34. [12a] M. Karpf, Ph. D. Thesis, Univ. of Stuttgart, 1995.
35. [12b] P. Fischer, R. Aichholz, U. Bolz, M. Juzu, S. Krimmer, Angew. Chem. 1990, 702, 439-441;
36. Angew. Chem. Int. Ed. Engl. 1990, 29, 427.
37. [12c] W. A. König, D. Ichein, T. Runge, I. Pforr, A. Krebs, J. High Res. Chromatogr. 1990, 13, 702.
38. [12d] W. A. König, Gas Chromatographic Enantiomer Separation with Modified Cyclodextrins, Hüthig Buch Verlag, Heidelberg, 1992.
39. D. Seebach, H.-O. Kalinowski, B. Bastani, G. Crass, H. Daum, H. Dörr, N. P. DuPreez, V. Ehrie, W. Langer, C. Nüssler, H.-A. Oei, M. Schmidt, Helv. Chim. Accta 1977, 60, 301-325.
40. M. Schmidt, R. Amstutz, G. Crass, D. Seebach, Chem. Ber. 1980, 113, 1691-1707.
41. D. Seebach, A. K. Beck, R. Imwinkelried, S. Roggo, A. Wonnacott, Helv. Chim. Acta 1987, 70, 954-974.
42. K. Nakayama, J. D. Rainier, Tetrahedron 1990, 46, 4165-4170.
43. In fact, the overall yield could be improved to 62% (from 38%).
44. [18a] P. Lombardi, Chem. Ind. (London), Nov. 5, 1990, 708.
45. [18b] S. Moss. Chem. Ind. (London). Feb. 21, 1994, 122.