Photochemical synthesis of prochiral dialkyl 3,3-dialkylcyclopropene-1,2-dicarboxylates with facial shielding substituents and related substrates

European Journal of Organic Chemistry

Volumn , Issue 24, 2001, Pages 4705-4732

  Hashmi, A Stephen K ^a   Grundl, Marc A ^a   Nass, Andreas Rivas ^a   Naumann, Frank ^a   Bats, Jan W ^a   Bolte, Michael ^a  

^a GOETHE UNIVERSITY   (Germany)

Author keywords

Alkynes; Cyclopropenes; Oxadiazolines; Pyrazoles; Strained molecules

Indexed keywords

ALKANE DERIVATIVE; ALKYNE; CARBOXYLIC ACID DERIVATIVE; CYCLOPROPENE 1,2 DICARBOXYLIC ACID DERIVATIVE; OXADIAZOLE DERIVATIVE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CRYSTAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; PHOTOCHEMISTRY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0035664747     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200112)2001:24<4705::AID-EJOC4705>3.0.CO;2-J     Document Type: Article

References (62)

1. [1a] A. S. K. Hashmi, F. Naumann, R. Probst, J. W. Bats, Angew. Chem. 1997, 109, 127-130;
2. Angew. Chem. Int. Ed. Engl. 1997, 36, 104-106.
3. [1b] A. S. K. Hashmi, F. Naumann, J. W. Bats, Chem. Ber./Recueil 1997, 130, 1457-1459.
4. [1c] A. S. K. Hashmi, F. Naumann, M. Bolte, A. Rivas Nass, J. Prakt. Chem. 1998, 340, 240-246.
5. A. S. K. Hashmi, F. Naumann, M. Bolte, Organometallics 1998, 17, 2385-2387.
6. A. S. K. Hashmi, F. Naumann, A. Rivas Nass, M. Bolte, J. W. Bats, Chem. Eur. J. 1999, 5, 2836-2844.
7. A. S. K. Hashmi, A. Rivas Nass, J. W. Bats, M. Bolte, Angew. Chem. 1999, 111, 3565-3567;
8. Angew. Chem. Int. Ed. 1999, 38, 3370-3373.
9. M. A. Grundl, Diploma Thesis, Johann Wolfgang Goethe-Universität Frankfurt, 1998.
10. M. S. Baird, H. Hopf, R. J. Bushby, Th. Schmidt, Methoden Org. Chem. (Houben-Weyl), 1997, vol. E17d, p. 2695-2780.
11. C. Dietrich-Buchecker, M. Franck-Neumann, Tetrahedron 1977, 33, 745-749 and 751-755.
12. A. C. Day, P. Raymond, R. M. Southam, M. C. Whiting, J. Chem. Soc., Chem. Commun. 1966, 467-469.
13. S. D. Andrews, A. C. Day, P. Raymond, M. C. Whiting, Org. Synth. 1971, 50, 27-30.
14. J. L. Charlton, G. Che, Tetrahedron Lett. 1994, 35, 6243-6246.
15. J. L. Charlton, G. Che, H. McColeman, Can. J. Chem. 1995, 73, 1454-1462.
16. P. Schnurrenberger, M. F. Züger, D. Seebach, Helv. Chim. Acta 1982, 65, 1197-1201.
17. 2), -154589 (8o), -154592 (9f), -154588 (12e), -154593 (12f), -154594 (13k), -154595 (16), -154605 (17),-154596 (18b), - 154597 (23b), -154604 (23d), -154606 (23c), -154607 (23g), - 154598 (24g), -154599 (27), -154608 (28), -154610 (29), -154600 (30), -154601 (33), -154602 (35), -154603 (34). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (internat.) + 44-1233/336-033; E-mail: deposit@ccdc.cam.ac.uk].
18. A. C. Larson D. F. Cromer, Acta Crystallogr., Sect. B 1973, 29, 1579-1583;
19. V. Benghiat, L. Leiserowitz, G. M. Schmidt, J. Chem. Soc., Perkin Trans. 2 1972, 1769-1772;
20. T. Goldberg, Acta Crystallogr., Sect. B 1975, 31, 754-762;
21. S. E. Evans, J. Trotter, V. C. Lee, Acta Crystallogr., Sect C 1988, 44, 878-880;
22. T. Güthner, U. Thewalt, J. Organomet. Chem. 1988, 350, 235-241;
23. I. Leban, A. Rupnik, Acta Crystallogr., Sect. C 1992, 48, 821-824.
24. R. Sustmann, H. Trill, Angew. Chem. 1972, 84, 888-889;
25. Angew. Chem. Int. Ed. Engl. 1972, 11, 838-840.
26. R. Sustmann, Tetrahedron Lett. 1971, 2717-2720
27. J. Van Alphen, Recl. Trav. Chim. Pays-Bas 1943, 62, 485-490;
28. J. van Alphen, Recl. Trav. Chim. Pays-Bas 1943, 62, 491-496;
29. R. Hüttel, K. Franke, H. Martin, J. Riedel, Chem. Ber. 1960, 93, 1433-1446
30. H. Durr, G. Klauck, K. Peters, H. G. von Schnering, Angew. Chem. 1983, 95, 321-321;
31. Angew. Chem. Int. Ed. Engl. 1983, 22, 332-333;
32. I. Leban, L. Golič, B. Stanovnik, M. Tišler, Acta Crystallogr., Sect. C 1987, 43, 1814-1816;
33. A. Stimac, B. Stanovnik, M. Tišler, L. Golič, Tetrahedron 1990, 46, 6915-6930.
34. M. W. Majchrzak, M. Békhazi, I. Tse-Sheepy, J. Warkentin, J. Org. Chem. 1989, 54, 1842-1845.
35. J. W. Bats, M. A. Grundl, A. S. K. Hashmi, Acta Crystallogr., Sect. A 1999, 55, 689-691.
36. P. D. Robinson, C. Y. Meyers, V. M. Kolb, Acta Crystallogr., Sect. C 1994, 50, 732-734.
37. A. R. Katritzky, H. M. Faid-Allah, H. Aghabozorg, G. J. Palenik, Chem. Scr. 1984, 23, 134-139;
38. A. Prakash, C. Calvo, A. M. Cameron, J. Warkentin, J. Cryst. Mol. Struct. 1973, 3, 71-78;
39. R. S. Dickson, G. D. Fallon, B. C. Bronwyn, B. W. Skelton, A. H. White, Inorg. Chim. Acta 1993, 212, 139-148.
40. E. A. Jefferson, J. Warkentin, J. Am. Chem. Soc. 1992, 114, 6318-6325.
41. J. W. Bats, M. A. Grundl, A. S. K. Hashmi, Acta Crystallogr., Sect. C 2001, 57, 208-210.
42. J. W. Bats, M. A. Grundl, A. S. K. Hashmi, Acta Crystallogr., Sect. C 2001, 57, 441-443.
43. A. Padwa, G. D. Kennedy, J. Am. Chem. Soc. 1983, 105, 137-139;
44. J. Org. Chem. 1984, 49, 4344-4352.
45. J. W. Bats, M. A. Grundl, A. S. K. Hashmi, Acta Crystallogr., Sect. C 2001, 57, 653-656.
46. D. Rewicki, C. Tuchscherer, Angew. Chem. 1972, 84, 31-32;
47. Angew. Chem. Int. Ed. Engl. 1972, 11, 44-45.
48. A. Padwa, S. I. Goldstein, Can. J. Chem. 1984, 62, 2506-2514.
49. P. Luger, C. Tuchscherer, M. Grosse, D. Rewicki, Chem. Ber. 1976, 109, 2596-2614.
50. E. LeGeoff, R. B. LaCount, Tetrahedron Lett. 1967, 2333-2335.
51. J. C. Kaver, H. E. Simmons, J. Org. Chem. 1968, 33, 2720-2726.
52. E. Winterfeldt, G. Giesler, Chem. Ber. 1968, 101, 4022-4031.
53. N. Schulte, M. H. Moller, U. Rodewald, E.-U. Würthwein, Chem. Ber. 1994, 127, 1287-1293.
54. M. B. Hocking, F. W. van der Voort Maarschalk, Can. J. Chem. 1994, 72, 2428-2442.
55. J. Newham, Chem. Rev. 1963, 63, 123-137.
56. B. M. Trost, M. K. Trost, J. Am. Chem. Soc. 1991, 113, 1850-1852.
57. C. G. Sims, D. Wege, Aust. J. Chem. 1995, 48, 469-490. Only 45% of 11e was obtained.
58. This compound has already been synthesized by a different route: F. E. Herkes, H. E. Simmons, J. Org. Chem. 1975, 40, 420-423.
59. L. Somogyi, Liebigs Ann. Chem. 1991, 1267-1271.
60. W. P. Ratchford, C. H. Fisher, J. Org. Chem. 1950, 15, 317-325.
61. A. Padwa, S. I. Goldstein, Can. J. Chem. 1984, 62, 2506-2514.
62. J. C. Kaver, H. E. Simmons, J. Org. Chem. 1968, 33, 2720-2726.