Titanium-mediated synthesis of bicyclic cyclopropylamines from unsaturated nitriles

Tetrahedron Letters

Volumn 44, Issue 12, 2003, Pages 2485-2487

  Laroche, Christophe ^a   Bertus, Philippe ^a   Szymoniak, Jan ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

Bicyclic compounds; Cyclizations; Cyclopropanes; Nitriles; Titanium

Indexed keywords

ALKENE DERIVATIVE; CYCLOPROPANE DERIVATIVE; NITRILE; REAGENT; TITANIUM;

ARTICLE; CYCLIZATION; CYCLOPROPANATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0037450916     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00325-3     Document Type: Article

References (25)

1. Salaün J. Top. Curr. Chem. 207:2000;1-67.
2. Pirrung M.C. Acc. Chem. Res. 32:1999;711-718.
3. See for example: (a) Abacavir: Daluge, S. M.; Martin, M. T.; Sickles, B. R.; Livingston, D. A. Nucleosides Nucleotides 2000, 19, 297-327; (b) MIV-150: Högberg, M.; Sahlberg, C.; Engelhardt, P.; Noréen, R.; Kangasmetsä, J.; Johansson, N. G.; Öberg, B.; Vrang, L.; Zhang, H.; Sahlberg, B.-L.; Unge, T.; Lövgren, S.; Fridborg, K.; Bäckbro, K. J. Med. Chem. 1999, 42, 4150-4160; (c) Trovafloxacine: Brighty, K. E.; Castaldi, M. J. Synlett 1996, 1097-1099; (d) Tranylcypromine: Fujita, T. J. Med. Chem. 1973, 16, 923-930.
4. See for example: (a) Abacavir: Daluge, S. M.; Martin, M. T.; Sickles, B. R.; Livingston, D. A. Nucleosides Nucleotides 2000, 19, 297-327; (b) MIV-150: Högberg, M.; Sahlberg, C.; Engelhardt, P.; Noréen, R.; Kangasmetsä, J.; Johansson, N. G.; Öberg, B.; Vrang, L.; Zhang, H.; Sahlberg, B.-L.; Unge, T.; Lövgren, S.; Fridborg, K.; Bäckbro, K. J. Med. Chem. 1999, 42, 4150-4160; (c) Trovafloxacine: Brighty, K. E.; Castaldi, M. J. Synlett 1996, 1097-1099; (d) Tranylcypromine: Fujita, T. J. Med. Chem. 1973, 16, 923-930.
5. See for example: (a) Abacavir: Daluge, S. M.; Martin, M. T.; Sickles, B. R.; Livingston, D. A. Nucleosides Nucleotides 2000, 19, 297-327; (b) MIV-150: Högberg, M.; Sahlberg, C.; Engelhardt, P.; Noréen, R.; Kangasmetsä, J.; Johansson, N. G.; Öberg, B.; Vrang, L.; Zhang, H.; Sahlberg, B.-L.; Unge, T.; Lövgren, S.; Fridborg, K.; Bäckbro, K. J. Med. Chem. 1999, 42, 4150-4160; (c) Trovafloxacine: Brighty, K. E.; Castaldi, M. J. Synlett 1996, 1097-1099; (d) Tranylcypromine: Fujita, T. J. Med. Chem. 1973, 16, 923-930.
6. See for example: (a) Abacavir: Daluge, S. M.; Martin, M. T.; Sickles, B. R.; Livingston, D. A. Nucleosides Nucleotides 2000, 19, 297-327; (b) MIV-150: Högberg, M.; Sahlberg, C.; Engelhardt, P.; Noréen, R.; Kangasmetsä, J.; Johansson, N. G.; Öberg, B.; Vrang, L.; Zhang, H.; Sahlberg, B.-L.; Unge, T.; Lövgren, S.; Fridborg, K.; Bäckbro, K. J. Med. Chem. 1999, 42, 4150-4160; (c) Trovafloxacine: Brighty, K. E.; Castaldi, M. J. Synlett 1996, 1097-1099; (d) Tranylcypromine: Fujita, T. J. Med. Chem. 1973, 16, 923-930.
7. Bertus P., Szymoniak J. Chem. Commun. 2001;1792-1793.
8. Bertus P., Szymoniak J. J. Org. Chem. 67:2002;3965-3968.
9. For reviews, see: (a) de Meijere, A.; Kozhushkov, S. I.; Savchenko, A. I. In Titanium and Zirconium in Organic Synthesis; Marek, I.; Ed.; Wiley-VCH: Weinheim, 2002; pp. 390-434; (b) Kulinkovich, O. G.; de Meijere, A. Chem. Rev. 2000, 100, 2789-2834.
10. For reviews, see: (a) de Meijere, A.; Kozhushkov, S. I.; Savchenko, A. I. In Titanium and Zirconium in Organic Synthesis; Marek, I.; Ed.; Wiley-VCH: Weinheim, 2002; pp. 390-434; (b) Kulinkovich, O. G.; de Meijere, A. Chem. Rev. 2000, 100, 2789-2834.
11. The ligand exchange methodology was first described by Kulinkovich et al., see: Kulinkovich O.G., Savchenko A.I., Sviridov S.V., Vasilevski D.A. Mendeleev Commun. 1993;230-231.
12. Lee J., Kang C.H., Kim H., Cha J.K. J. Am. Chem. Soc. 118:1996;291-292.
13. U J.S., Lee J., Cha J.K. Tetrahedron Lett. 38:1997;5233-5236.
14. Kasatkin A., Sato F. Tetrahedron Lett. 36:1995;6079-6082.
15. Kasatkin A., Kobayashi K., Okamoto S., Sato F. Tetrahedron Lett. 37:1996;1849-1852.
16. Okamoto S., Iwakubo M., Kobayashi K., Sato F. J. Am. Chem. Soc. 119:1997;6984-6990.
17. Lee J., Cha J.K. J. Org. Chem. 62:1997;1584-1585.
18. Cao B., Xiao D., Joullié M.M. Org. Lett. 1:1999;1799-1801.
19. Gensini M., Kozhushkov S.I., Yufit D., Howard J.A.K., Es-Sayed M., de Meijere A. Eur. J. Org. Chem. 2002;2499-2507.
20. In the paper cited in Ref. 12, the reaction of 1 with cyclohexylmagnesium chloride led only to traces of product 3, under the conditions described in Ref. 4. Moreover, the bicyclo[4.1.0]heptane framework could not be formed from the corresponding nitriles.
21. 2 were tried, but without improving the yield of 3.
22. This is in contrast to the reaction employing esters or amides. In the latter cases, the Grignard reagent is generally used in excess. See Refs. 8-12.
23. Several attempts to prepare cyclopropylamines intermoleculary from nitriles and alkenes (styrene, 1-octene) via ligand exchange were unsuccessful.
24. 2 (0.25 mL, 2 mmol) was added at once. Stirring was continued over a period of 30 min. A solution of 10% NaOH (ca. 1 mL) was added and the mixture was extracted with ether. The combined ether layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting crude material was purified by flash chromatography on silica gel.
25. +·, 10), 187 (10), 161 (11), 132 (15), 120 (25), 91 (100).