Highly stereoselective synthesis of cyclopropylphosphonates catalyzed by chiral Ru(II)-pheox complex

Organic Letters

Volumn 16, Issue 11, 2014, Pages 3012-3015

  Chanthamath, Soda ^a   Ozaki, Seiya ^a   Shibatomi, Kazutaka ^a   Iwasa, Seiji ^a  

^a TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COORDINATION COMPOUND; CYCLOPROPANE DERIVATIVE; ORGANOPHOSPHORUS COMPOUND; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; COORDINATION COMPLEXES; CYCLOPROPANES; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; RUTHENIUM; STEREOISOMERISM;

EID: 84902119360     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501135p     Document Type: Article

References (27)

1. Midura, W. H.; Krysiak, J. A.; Mikołajczyk, M. Tetrahedron: Asymmetry 2003, 14, 1245-1249
2. Pyun, H.-J.; Clarke, M. O.; Cho, A.; Casarez, A.; Ji, M.; Fardis, M.; Pastor, R.; Sheng, X. C.; Kim, C. U. Tetrahedron Lett. 2012, 53, 2360-2363
3. Midura, W. H.; Krysiak, J.; Rzewnicka, A.; Supeł, A.; Łyżwa, P.; Ewas, A. M. Tetrahedron 2013, 69, 730-737
4. Devreux, V.; Wiesner, J.; Goeman, J. L.; Eycken, J. V.; Jomaa, H.; Calenbergh, S. V. J. Med. Chem. 2006, 49, 2656-2660
5. Lewis, R. T.; Motherwell, W. B. Tetrahedron Lett. 1988, 29, 5033-5036
6. Hirao, T.; Hagihara, M.; Ohshiro, Y.; Agawa, T. Synthesis 1984, 1, 60-61
7. Dappen, M. S.; Pellicciari, R.; Natalini, B.; Monahan, J. B.; Chiorri, C.; Cordi, A. A. J. Med. Chem. 1991, 34, 161-168
8. Lewis, R. T.; Motherwell, W. B.; Shipman, M.; Slawin, A. M. Z.; Williams, D. J. Tetrahedron 1995, 51, 3289-3302
9. Yan, Z.; Zhou, S.; Kern, E. R.; Zemlicka, J. Tetrahedron 2006, 62, 2608-2615
10. Davi, M.; Lebel, H. Chem. Commun. 2008, 4974-4976
11. Krawczyk, H.; Wasek, K.; Kedzia, J.; Wojciechowski, J.; Wolf, W. M. Org. Biomol. Chem. 2008, 6, 308-318
12. Amori, L.; Serpi, M.; Marinozzi, M.; Costantino, G.; Diaz, M. G.; Mermit, M. B.; Thomsen, C.; Pellicciari, R. Dokl. Akad. Nauk 2013, 450, 547-552
13. Maux, P. L.; Abrunhosa, I.; Berchel, M.; Simonneaux, G.; Gulea, M.; Masson, S. Tetrahedron: Asymmetry 2004, 15, 2569-2573
14. Amori, L.; Serpi, M.; Marinozzi, M.; Costantino, G.; Diaz, M. G.; Mermit, M. B.; Thomsen, C.; Pellicciari, R. Bioorg. Med. Chem. Lett. 2006, 16, 196-199
15. Midura, W. H.; Sobczak, A.; Paluch, P. Tetrahedron Lett. 2013, 54, 223-226
16. Charette, A. B.; Bouchard, J.-E. Can. J. Chem. 2005, 83, 533-542
17. Lindsay, V. N. G.; Fiset, D.; Gritsch, P. J.; Azzi, S.; Charette, A. B. J. Am. Chem. Soc. 2013, 135, 1463-1470
18. Ferrand, Y.; Maux, P. L.; Simonneaux, G. Org. Lett. 2004, 6, 3211-3213
19. Paul-Roth, C.; Montigny, F. D.; Rethoré, G.; Simonneaux, G.; Gulea, M.; Masson, S. J. Mol. Catal. A: Chem. 2003, 201, 79-91
20. Abu-Elfotoh, A.-M.; Phomkeona, K.; Shibatomi, K.; Iwasa, S. Angew. Chem., Int. Ed. 2010, 49, 8439-8443
21. Chanthamath, S.; Phomkeona, K.; Shibatomi, K.; Iwasa, S. Chem. Commun. 2012, 48, 7750-7752
22. Chanthamath, S.; Thongjareun, S.; Shibatomi, K.; Iwasa, S. Tetrahedron Lett. 2012, 53, 4862-4865
23. Abu-Elfotoh, A.-M.; Nguyen, D. P. T.; Chanthamath, S.; Phomkeona, K.; Shibatomi, K.; Iwasa, S. Adv. Synth. Catal. 2012, 354, 3435-3439
24. Chanthamath, S.; Nguyen, D. T.; Shibatomi, K.; Iwasa, S. Org. Lett. 2013, 15, 772-775
25. Chanthamath, S.; Takaki, S.; Shibatomi, K.; Iwasa, S. Angew. Chem., Int. Ed. 2013, 52, 5818-5821
26. 3) for 1 R, 2 R -isomer, see: Krawczyk, H.; Wasek, K.; Kedzia, J. Synthesis 2009, 9, 1473-1476
27. Hah, J. H.; Gil, J. M.; Oh, D. Y. Tetrahedron Lett. 1999, 40, 8235-8238