Chemoselective Addition of Halomethyllithiums to Functionalized Isatins:A Straightforward Access to Spiro-Epoxyoxindoles

Advanced Synthesis and Catalysis

Volumn 358, Issue 2, 2016, Pages 172-177

  Pace, Vittorio ^a   Castoldi, Laura ^a   Mamuye, Ashenafi Damtew ^a,b   Langer, Thierry ^a   Holzer, Wolfgang ^a  

^a UNIVERSITY OF VIENNA   (Austria)

^b UNIVERSITY OF SASSARI   (Italy)

Author keywords

carbenoids; chemoselectivity; epoxidation; Grignard reaction; homologation

Indexed keywords

EID: 84957428465     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201500840     Document Type: Article

References (93)

1. C. Marti, E. M. Carreira, Eur. J. Org. Chem. 2003, 2209-2219;
2. F. Zhou, Y.-L. Liu, J. Zhou, Adv. Synth. Catal. 2010, 352, 1381-1407.
3. G. S. Singh, Z. Y. Desta, Chem. Rev. 2012, 112, 6104-6155;
4. R. Rios, Chem. Soc. Rev. 2012, 41, 1060-1074;
5. N. R. Ball-Jones, J. J. Badillo, A. K. Franz, Org. Biomol. Chem. 2012, 10, 5165-5181.
6. L. Wang, Y. Su, X. Xu, W. Zhang, Eur. J. Org. Chem. 2012, 6606-6611;
7. A. K. Yudin, Aziridines and Epoxides in Organic Synthesis, Wiley-VCH, Weinheim, 2006;
8. G. S. Singh, K. Mollet, M. D′hooghe, N. DeKimpe, Chem. Rev. 2013, 113, 1441-1498.
9. V. Schulz, M. Davoust, M. Lemarié, J.-F. Lohier, J. SopkovadeOliveiraSantos, P. Metzner, J.-F. Brière, Org. Lett. 2007, 9, 1745-1748.
10. A. Boucherif, Q.-Q. Yang, Q. Wang, J.-R. Chen, L.-Q. Lu, W.-J. Xiao, J. Org. Chem. 2014, 79, 3924-3929.
11. Y. Kuang, Y. Lu, Y. Tang, X. Liu, L. Lin, X. Feng, Org. Lett. 2014, 16, 4244-4247.
12. F. Arndt, B. Eistert, W. Ender, Ber. dtsch. chem. Ges. 1929, 62, 44-56.
13. L. Capuano, M. Welter, Chem. Ber. 1968, 101, 3671-3678.
14. B. Alcaide, P. Almendros, C. Aragoncillo, G. Gõmez-Campillos, M. Arnõ, L. R. Domingo, ChemPlusChem 2012, 77, 563-569.
15. M. S. Chodnekar, A. F. Crowther, W. Hepworth, R. Howe, B. J. McLoughlin, A. Mitchell, B. S. Rao, R. P. Slatcher, L. H. Smith, M. A. Stevens, J. Med. Chem. 1972, 15, 49-57.
16. P. D. Kennewell, D. J. Miller, R. M. Scrowston, R. Westwood, J. Chem. Soc. Miniprint 1995, 10, 2380-2388.
17. M. Chouhan, K. R. Senwar, R. Sharma, V. Grover, V. A. Nair, Green Chem. 2011, 13, 2553-2560.
18. S. Hajra, S. Maity, R. Maity, Org. Lett. 2015, 17, 3430-3433.
19. E. J. Corey, M. Chaykovsky, J. Am. Chem. Soc. 1962, 84, 867-868;
20. Y. G. Gololobov, A. N. Nesmeyanov, V. P. lysenko, I. E. Boldeskul, Tetrahedron 1987, 43, 2609-2651.
21. I. Gorokhovik, L. Neuville, J. Zhu, Org. Lett. 2011, 13, 5536-5539.
22. J. F. M. daSilva, S. J. Garden, A. C. Pinto, J. Braz. Chem. Soc. 2001, 12, 273-324;
23. A. D. Mamuye, S. Monticelli, L. Castoldi, W. Holzer, V. Pace, Green Chem. 2015, 17, 4194-4197.
24. G. Boche, J. C. W. Lohrenz, Chem. Rev. 2001, 101, 697-756;
25. V. Capriati, S. Florio, Chem. Eur. J. 2010, 16, 4152-4162;
26. M. Braun, in: The Chemistry of Organolithium Compounds, Vol. 1, (Eds.:, Z. Rappoport, I. Marek,), John Wiley and Sons, Chichester, 2004, pp 829-900;
27. V. Pace, Aust. J. Chem. 2014, 67, 311-313;
28. R. H. V. Nishimura, V. E. Murie, R. A. Soldi, J. L. C. Lopes, G. C. Clososki, J. Braz. Chem. Soc. 2015, 26, 2175-2188.
29. V. Pace, L. Castoldi, W. Holzer, J. Org. Chem. 2013, 78, 7764-7770;
30. V. Pace, L. Castoldi, W. Holzer, Chem. Commun. 2013, 49, 8383-8385;
31. V. Pace, W. Holzer, G. Verniest, A. R. Alcántara, N. DeKimpe, Adv. Synth. Catal. 2013, 355, 919-926;
32. V. Pace, L. Castoldi, W. Holzer, Adv. Synth. Catal. 2014, 356, 1761-1766;
33. V. Pace, L. Castoldi, A. D. Mamuye, W. Holzer, Synthesis 2014, 46, 2897-2909;
34. A. D. Mamuye, L. Castoldi, U. Azzena, W. Holzer, V. Pace, Org. Biomol. Chem. 2015, 13, 1969-1973.
35. R. Tarhouni, B. Kirschleger, M. Rambaud, J. Villieras, Tetrahedron Lett. 1984, 25, 835-838;
36. J. Barluenga, B. Baragaña, J. M. Concellõn, J. Org. Chem. 1995, 60, 6696-6699;
37. J. M. Concellõn, H. Rodríguez-Solla, C. Simal, Org. Lett. 2008, 10, 4457-4460;
38. J. M. Concellõn, H. Rodríguez-Solla, P. L. Bernad, C. Simal, J. Org. Chem. 2009, 74, 2452-2459;
39. D. C. Kapeller, F. Hammerschmidt, J. Am. Chem. Soc. 2008, 130, 2329-2335;
40. D. C. Kail, P. MalovaKrizkova, A. Wieczorek, F. Hammerschmidt, Chem. Eur. J. 2014, 20, 4086-4091;
41. A. Wieczorek, F. Hammerschmidt, J. Org. Chem. 2012, 77, 10021-10034;
42. T. Boddaert, C. François, L. Mistico, O. Querolle, L. Meerpoel, P. Angibaud, M. Durandetti, J. Maddaluno, Chem. Eur. J. 2014, 20, 10131-10139;
43. R. Lhermet, M. Ahmad, C. Fressigné, B. Silvi, M. Durandetti, J. Maddaluno, Chem. Eur. J. 2014, 20, 10249-10254;
44. P. R. Blakemore, S. P. Marsden, H. D. Vater, Org. Lett. 2006, 8, 773-776;
45. P. R. Blakemore, M. S. Burge, J. Am. Chem. Soc. 2007, 129, 3068-3069;
46. A. L. Barsamian, P. R. Blakemore, Organometallics 2012, 31, 19-22;
47. C. R. Emerson, L. N. Zakharov, P. R. Blakemore, Chem. Eur. J. 2013, 19, 16342-16356;
48. S. Balieu, G. E. Hallett, M. Burns, T. Bootwicha, J. Studley, V. K. Aggarwal, J. Am. Chem. Soc. 2015, 137, 4398-4403;
49. P. J. Unsworth, D. Leonori, V. K. Aggarwal, Angew. Chem. 2014, 126, 10004-10008;
50. Angew. Chem. Int. Ed. 2014, 53, 9846-9850;
51. D. S. Matteson, D. Majumdar, J. Am. Chem. Soc. 1980, 102, 7588-7590;
52. D. S. Matteson, D. Majumdar, Organometallics 1983, 2, 1529-1535;
53. K. M. Sadhu, D. S. Matteson, Tetrahedron Lett. 1986, 27, 795-798;
54. C. Kupper, S. Molitor, V. H. Gessner, Organometallics 2014, 33, 347-353;
55. S. Molitor, J. Becker, V. H. Gessner, J. Am. Chem. Soc. 2014, 136, 15517-15520;
56. S. Molitor, K.-S. Feichtner, C. Kupper, V. H. Gessner, Chem. Eur. J. 2014, 20, 10752-10762;
57. S. Molitor, V. H. Gessner, Synlett 2015, 26, 861-865;
58. J. A. Bull, T. Boultwood, T. A. Taylor, Chem. Commun. 2012, 48, 12246-12248;
59. T. Boultwood, D. P. Affron, A. D. Trowbridge, J. A. Bull, J. Org. Chem. 2013, 78, 6632-6647;
60. T. Boultwood, D. P. Affron, J. A. Bull, Tetrahedron 2015, 71, 4949-4957;
61. D. Savoia, G. Alvaro, R. DiFabio, A. Gualandi, C. Fiorelli, J. Org. Chem. 2006, 71, 9373-9381.
62. L. Degennaro, F. Fanelli, A. Giovine, R. Luisi, Adv. Synth. Catal. 2015, 357, 21-27.
63. W. Kirmse, Angew. Chem. 1965, 77, 1-10;
64. Angew. Chem. Int. Ed. Engl. 1965, 4, 1-10.
65. N. A. Afagh, A. K. Yudin, Angew. Chem. 2010, 122, 270-320;
66. Angew. Chem. Int. Ed. 2010, 49, 262-310.
67. S. Nahm, S. M. Weinreb, Tetrahedron Lett. 1981, 22, 3815-3818;
68. S. Balasubramaniam, I. S. Aidhen, Synthesis 2008, 3707-3738;
69. V. Pace, W. Holzer, B. Olofsson, Adv. Synth. Catal. 2014, 356, 3697-3736;
70. V. Pace, W. Holzer, Aust. J. Chem. 2013, 507-510.
71. R. H. V. Nishimura, F. T. Toledo, J. L. C. Lopes, G. C. Clososki, Tetrahedron Lett. 2013, 54, 287-290;
72. R. H. V. Nishimura, V. E. Murie, R. A. Soldi, G. C. Clososki, Synthesis 2015, 47, 1455-1460.
73. J. M. Concellõn, H. Cuervo, R. Fernández-Fano, Tetrahedron 2001, 57, 8983-8987.
74. T. Onishi, N. Hirose, T. Nakano, M. Nakazawa, K. Izawa, Tetrahedron Lett. 2001, 42, 5883-5885;
75. T. Onishi, T. Nakano, N. Hirose, M. Nakazawa, K. Izawa, Tetrahedron Lett. 2001, 42, 5887-5890;
76. W. Gohring, S. Gokhale, H. Hilpert, F. Roessler, M. Schlageter, P. Vogt, Chimia 1996, 50, 532-537.
77. M. G. Suero, E. D. Bayle, B. S. L. Collins, M. J. Gaunt, J. Am. Chem. Soc. 2013, 135, 5332-5335;
78. A. J. Walkinshaw, W. Xu, M. G. Suero, M. J. Gaunt, J. Am. Chem. Soc. 2013, 135, 12532-12535;
79. E. Cahard, N. Bremeyer, M. J. Gaunt, Angew. Chem. Int. Ed. 2013, 52, 9284-9288;
80. E. A. Merritt, B. Olofsson, Angew. Chem. 2009, 121, 9214-9234;
81. Angew. Chem. Int. Ed. 2009, 48, 9052-9070.
82. E. Cahard, H. P. J. Male, M. Tissot, M. J. Gaunt, J. Am. Chem. Soc. 2015, 137, 7986-7989.
83. A. V. Bogdanov, V. F. Mironov, L. I. Musin, R. Z. Musin, Synthesis 2010, 3268-3270.
84. V. Pace, F. Martínez, M. Fernández, J. V. Sinisterra, A. R. Alcántara, Org. Lett. 2007, 9, 2661-2664;
85. V. Pace, F. Martínez, M. Fernández, J. V. Sinisterra, A. R. Alcántara, Adv. Synth. Catal. 2009, 351, 3199-3206;
86. V. Pace, J. V. Sinisterra, A. R. Alcántara, Curr. Org. Chem. 2010, 14, 2384-2408;
87. V. Pace, L. Castoldi, W. Holzer, Tetrahedron Lett. 2012, 53, 967-972.
88. Y. Masaki, H. Arasaki, M. Iwata, Chem. Lett. 2003, 32, 4-5;
89. H. Arasaki, M. Iwata, D. Nishimura, A. Itoh, Y. Masaki, Synlett 2004, 546-548;
90. A. Kirrmann, R. Nouri-Bimorghi, Bull. Soc. Chim. Fr. 1968, 3213-3220;
91. V. A. Mamedov, I. A. Litvinov, O. N. Kataeva, I. K. Rizvanov, I. A. Nuretdinov, Monatsh. Chem. 1994, 125, 1427-1435;
92. K.-i. Sato, T. Sekiguchi, T. Hozumi, T. Yamazaki, S. Akai, Tetrahedron Lett. 2002, 43, 3087-3090.
93. See the Supporting Information.