α-Lithiated Aryl Benzyl Ethers: Inhibition of [1,2]-Wittig Rearrangement and Application to the Synthesis of Benzo[b]furan Derivatives

Organic Letters

Volumn 17, Issue 18, 2015, Pages 4416-4419

  Velasco, Rocío ^a   Feberero, Claudia ^a   Sanz, Roberto ^a  

^a UNIVERSITY OF BURGOS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84941919286     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b01964     Document Type: Article

References (36)

1. Wittig, G.; Löhmann, L. Justus Liebigs Ann. Chem. 1942, 550, 260-268 10.1002/jlac.19425500117
2. Sawyer, J. S.; Kucerovy, A.; Macdonald, T. L.; McGarvey, G. J. J. Am. Chem. Soc. 1988, 110, 842-853 10.1021/ja00211a024
3. Marshall, J. A. The Wittig Rearrangement. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, pp 975-1014.
4. Schöllkopf, U. Angew. Chem., Int. Ed. Engl. 1970, 9, 763-773 10.1002/anie.197007631
5. Garst, J. F.; Smith, C. D. J. Am. Chem. Soc. 1976, 98, 1526-1537 10.1021/ja00422a041
6. Tomooka, K.; Yamamoto, H.; Nakai, T. Liebigs Ann./Recueil 1997, 1997, 1275-1281 10.1002/jlac.199719970703
7. Tomooka, K.; Yamamoto, K.; Nakai, T. Angew. Chem., Int. Ed. 1999, 38, 3741-3743 10.1002/(SICI)1521-3773(19991216)38:24<3741::AID-ANIE3741>3.0.CO;2-5
8. Nakano, T.; Soeta, T.; Endo, K.; Inomata, K.; Ukaji, Y. J. Org. Chem. 2013, 78, 12654-12661 10.1021/jo402272r
9. Azzena, U.; Demartis, S.; Fiori, M. G.; Melloni, G.; Pisano, L. Tetrahedron Lett. 1995, 36 (31) 5641-5644 10.1016/0040-4039(95)01035-G
10. Eisch, J. J.; Kovacs, C. A.; Rhee, S.-G. J. Organomet. Chem. 1974, 65, 289-301 10.1016/S0022-328X(00)82263-9
11. Yang, J.; Dudley, G. B. J. Org. Chem. 2009, 74, 7998-8000 10.1021/jo901707x
12. Gao, G.; Gu, F.-L.; Jiang, J.-X.; Jiang, K.; Sheng, C.-Q.; Lai, G.-Q.; Xu, L.-W. Chem.-Eur. J. 2011, 17, 2698-2703 10.1002/chem.201003111
13. Barluenga, J.; Fañanás, F. J.; Sanz, R.; Marcos, C.; Trabada, M. Org. Lett. 2002, 4, 1587-1590 10.1021/ol0258029
14. Sanz, R.; Miguel, D.; Martínez, A.; Pérez, A. J. Org. Chem. 2006, 71, 4024-4027 10.1021/jo060271d
15. By study of the o-lithiation of benzyl fluorophenyl ethers, a partial metalation of the benzylic position of 1a was observed: Chodakowski, J.; Klis̈, T.; Serwatowski, J. Tetrahedron Lett. 2005, 46, 1963-1965 10.1016/j.tetlet.2005.02.006
16. De Luca, L.; Nieddu, G.; Porcheddu, A.; Giacomelli, G. Curr. Med. Chem. 2009, 16, 1-20 10.2174/092986709787002826
17. Yeung, K.-S.; Yang, Z.; Peng, X.-S.; Hou, X.-L. Prog. Heterocycl. Chem. 2011, 22, 181-216 10.1016/S0959-6380(11)22007-5
18. Nakamura, I.; Mizushima, Y.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 15022-15023 10.1021/ja055202f
19. Fürstner, A.; Davies, P. W. J. Am. Chem. Soc. 2005, 127, 15024-15025 10.1021/ja055659p
20. Sakiyama, N.; Noguchi, K.; Tanaka, K. Angew. Chem., Int. Ed. 2012, 51, 5976-5980 10.1002/anie.201201186
21. Shen, Z.; Dong, V. M. Angew. Chem., Int. Ed. 2009, 48, 784-786 10.1002/anie.200804854
22. Ma, X.; Wu, F.; Yi, X.; Wang, H.; Chen, W. Chem. Commun. 2015, 51, 6862-6865 10.1039/C5CC01271F
23. Hu, M.; Song, R.-J.; Li, J.-H. Angew. Chem., Int. Ed. 2015, 54, 608-612 10.1002/anie.201408978
24. Kanazawa, C.; Goto, K.; Terada, M. Chem. Commun. 2009, 5248-5250 10.1039/b913588j
25. Hu, J.; Wu, L.-Y.; Wang, X.-C.; Hu, Y.-Y.; Niu, Y.-N.; Liu, X.-Y.; Yang, S.; Liang, Y.-M. Adv. Synth. Catal. 2010, 352, 351-356 10.1002/adsc.200900649
26. Chen, P.-Y.; Wang, T.-P.; Huang, K.-S.; Kao, C.-L.; Tsai, J.-C.; Wang, E.-C. Tetrahedron 2011, 67, 9291-9297 10.1016/j.tet.2011.09.144
27. Grimaldi, T. B.; Back, D. F.; Zeni, G. J. Org. Chem. 2013, 78, 11017-11031 10.1021/jo4020062
28. Fañanás, F. J.; Sanz, R. Intramolecular Carbolithiation Reactions. In The Chemistry of Organolithium Compounds; Rappoport, Z.; Marek, I., Eds.; The Chemistry of Functional Groups; Rappoport, Z., Series Ed.; Wiley & Sons: Chichester, 2006; Vol. 2, Chapter 4, pp 295-379.
29. Barluenga, J.; Fañanás, F. J.; Sanz, R.; Marcos, C. Org. Lett. 2002, 4, 2225-2228 10.1021/ol026078x
30. Barluenga, J.; Fañanás, F. J.; Sanz, R.; Marcos, C. Chem.-Eur. J. 2005, 11, 5397-5407 10.1002/chem.200500377
31. Sanz, R.; Ignacio, J. M.; Rodríguez, M. A.; Fañanás, F. J.; Barluenga, J. Chem.-Eur. J. 2007, 13, 4998-5008 10.1002/chem.200601863
32. Bailey, W. F.; Ovaska, T. V. J. Am. Chem. Soc. 1993, 115, 3080-3090 10.1021/ja00061a006
33. Fressigné, C.; Girard, A.-L.; Durandetti, M.; Maddaluno, J. Angew. Chem., Int. Ed. 2008, 47, 891-893 10.1002/anie.200704139
34. Lhermet, R.; Ahmad, M.; Fressigné, C.; Durandetti, M.; Maddaluno, J. Chem.-Eur. J. 2014, 20, 10249-10254 10.1002/chem.201403605
35. Fressigné, C.; Lhermet, R.; Girard, A.-L.; Durandetti, M.; Maddaluno, J. J. Org. Chem. 2013, 78, 9659-9669 10.1021/jo4012893
36. Lhermet, R.; Ahmad, M.; Hauduc, C.; Fressigné, M.; Durandetti, M.; Maddaluno, J. Chem.-Eur. J. 2015, 21, 8105-8111 10.1002/chem.201500201