Intramolecular addition of γ-chloro carbanions to electrophilic groups: Synthesis of tricyclic tetrahydrofurans, pyrrolidines, and cyclopentanes

European Journal of Organic Chemistry

Volumn , Issue 10, 2010, Pages 1885-1894

  Wojtasiewicz, Anna ^a   Barbasiewicz, Michal ^a   Ma̧kosza, Mieczyslaw ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

Aldol reactions; Carbanions; Cyclization; Nucleophilic substitution; Polycycles

Indexed keywords

EID: 77949817733     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200901131     Document Type: Article

References (25)

1. S. Gronert, K. Azizian, M. A. Friedman, J. Am. Chem. Soc. 1998, 120, 3220-3226.
2. U. Habusha, E. Rozental, S. Hoz, J. Am. Chem. Soc. 2002, 124, 15006-15011.
3. B. Zwanenburg, N. De Kimpe in Carbocyclic Three-Membered Ring Compounds (Ed.: A. de Meijere), 4th ed., Thieme, Stuttgart, 1996, vol.E17a, pp. 29-40.
4. M. Ma̧kosza, M. Judka, Chem. Eur. J. 2002, 8, 4234-4240.
5. M. Barbasiewicz, M. Judka, M. Makosza, Russ. Chem. Bull. Int. Ed. 2004, 53, 1846-1858.
6. M. Ma̧kosza, M. Judka, Synlett 2004, 4, 717-719.
7. M. Ma̧kosza, M. Judka, Helv. Chim. Acta 2005, 88, 1676-1.68.1.
8. M. Ma̧kosza, M. Barbasiewicz, D. Krajewski, Org. Lett. 2005, 7, 2945-2948.
9. M. Ma̧kosza, A. Wojtasiewicz, Phosphorus Sulfur Silicon. Relat. Elem. 2009, 184, 857-864.
10. M. Barbasiewicz, M. Ma̧kosza, Synthesis 2006, 1190-1194.
11. A. Brandt, M. Śniežek, A. Wojtasiewicz, M. Ma̧kosza, Tetrahedron, accepted.
12. For other developments in the field, see: a) N. Baricordi, S. Benetti, G. Biondini, C. De Risi, G. P. Pollini, Tetrahedron Lett. 2004, 45, 1373-1375;
13. b) F. F. Fleming, V. Gudipati, O. W Steward, J. Org. Chem. 2003, 68, 3943-3946;
14. c) M. Smet, C. van Oosterwijck, K. van. Hecke, L. van Meervelt, A. Vandendriessche, W. Dehaen, Synlett 2004, 2388-2390;
15. d) A. Hassner, A. Laxer, E. Ghera, Arkivoc 2002, 8, 157-165;
16. e) A. Hassner, D. Usak, R. Rumareswaran, O. Friedman, Eur. J. Org. Chem. 2004, 2421-2426;
17. f) I. Shibata, H. Yamasaki, A. Baba, H. Matsuda, J. Org. Chem. 1992, 57, 6909-6914; for methods where γ-haloenolates are prepared by Lewis acid catalyzed opening of activated cyclopropanes and trapped in situ with electrophiles, see:
18. g) Z. Han, S. Uehira, T. Tsuritani, H. Shinokubo, K. Oshima, Tetrahedron 2001, 57, 987-995;
19. h) C. Timmons, D. Chen, J. F. Cannon, A. D. Headiey, G. Li, Org. Lett. 2004, 6, 2075-2078;
20. i) P. B. Alper, C. Meyers, A. Lerchner, D. R. Siegel, E. M. Carreira, Angew. Chem. Int. Ed. 1999, 38, 3186-3189;
21. j) C. A. Carson, M. A. Kerr, Chem. Soc. Rev. 2009, 38, 30513060 (review of applications of cyclopropane ring-opening methods in natural products synthesis).
22. a) K. Bowden, A. M. Last, J. Chem. Soc. D 1970, 1315-1316;
23. b) K. Bowden, Chem. Soc. Rev. 1995, 24, 431-435 (review).
24. O. O. Mamaeva, F. M. Stoyanovich, M. M. Krayushkin, Russ. Chem. Bull. 1989, 38, 1914-1923.
25. When the reaction of 15 was quenched with 10% aqueous HC1 and heated at reflux for 30 min, 13c (90%) was isolated. [16] The reaction of 16 conducted in EtOH was very unselective; thus, only limited mechanistic conclusions are available in this case.