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Synlett 2013; 24(1): 29-32
DOI: 10.1055/s-0032-1317746
DOI: 10.1055/s-0032-1317746
letter
Catalytic Asymmetric Cyclopropanation with Diazooxindole
Further Information
Publication History
Received: 12 October 2012
Accepted after revision: 12 November 2012
Publication Date:
11 December 2012 (online)

Abstract
The first catalytic asymmetric cyclopropanation using styrene and diazooxindole was achieved with Rh2(S-PTTL)4. The reaction proceeded smoothly with 1 mol% catalyst loading to provide a good yield of the biologically important spiro-cyclopropyloxindole product with moderate to good enantioselectivity and excellent diastereoselectivity.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References
- 1 Bindra JS. The Alkaloids . Vol. 14. Manske RH. F. Academic Press; New York: 1973: 84
- 2a Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748 ; Angew. Chem. 2007, 119, 8902
- 2b Marti C, Carreira EM. Eur. J. Org. Chem. 2003; 2209
- 2c Trost BM, Brennan MK. Synthesis 2009; 3003
- 3a Cui CB, Kakeya H, Osada H. Tetrahedron 1996; 52: 12651
- 3b Cui CB, Kakeya H, Osada H. J. Antibiot. 1996; 49: 832
- 4a Ding K, Lu Y, Nikolovska-Coleska Z, Qiu S, Ding Y, Gao W, Stuckey J, Krajewski K, Roller PP, Tomita Y, Parrish DA, Deschamps JR, Wang S. J. Am. Chem. Soc. 2005; 127: 10130
- 4b Ding K, Lu Y, Nikolovska-Coleska Z, Wang G, Qiu S, Shangary S, Gao W, Qin D, Stuckey J, Krajewski K, Roller PP, Wang S. J. Med. Chem. 2006; 49: 3432
- 4c Shangary S, Qin D, McEachern D, Liu M, Miller RS, Qiu S, Nikolovska-Coleska Z, Ding K, Wang G, Chen J, Bernard D, Zhang J, Lu Y, Gu Q, Shah RB, Pienta KJ, Ling X, Kang S, Guo M, Sun Y, Yang D, Wang S. Proc. Natl. Acad. Sci. U.S.A. 2008; 105: 3933
- 5a Stratmann K, Moore RE, Bonjouklian R, Deeter JB, Patterson GM. L, Shaffer S, Smith CD, Smitka TA. J. Am. Chem. Soc. 1994; 116: 9935
- 5b Jimenez JI, Huber U, Moore RE, Patterson GM. L. J. Nat. Prod. 1999; 62: 569
- 6a Baran PS, Richter JM. J. Am. Chem. Soc. 2005; 127: 15394
- 6b Reisman SE, Ready JM, Hasuoka A, Smith CJ, Wood JL. J. Am. Chem. Soc. 2006; 128: 1448
- 7a Jiang T, Kuhen KL, Wolff K, Yin H, Bieza K, Caldwell J, Bursulaya B, Wu TY.-H, He Y. Bioorg. Med. Chem. Lett. 2006; 16: 2105
- 7b Jiang T, Kuhen KL, Wolff K, Yin H, Bieza K, Caldwell J, Bursulaya B, Tuntland T, Zhang K, Karanewsky D, He Y. Bioorg. Med. Chem. Lett. 2006; 16: 2109
- 8a Dandia A, Singh R, Saha M, Shivpuri A. Pharmazie 2002; 57: 602
- 8b Zhang H.-P, Kamano Y, Ichihara Y, Kizu H, Komiyama K, Itokawa H, Pettit GR. Tetrahedron 1995; 51: 5523
- 8c Kamano Y, Zhang H.-P, Ichihara Y, Kizu H, Komiyama K, Pettit GR. Tetrahedron Lett. 1995; 36: 2783
- 9a Muthusamy S, Guanathan C. Synlett 2003; 1599
- 9b Chen S, Ma J, Wang J. Tetrahedron Lett. 2008; 49: 6781 ; see also ref. 7 and 10
- 10a Muthusamy S, Gunanathan C, Nethaji M. Synlett 2004; 639
- 10b Muthusamy S, Gunanathan C, Nethaji M. J. Org. Chem. 2004; 69: 5631
- 10c Schulz V, Davoust M, Lemari M, Lohier J.-F, Santos JS. O, Metzner P, Brire J.-F. Org. Lett. 2007; 9: 1745
- 10d Muthusamy S, Karikalan T, Suresh E. Tetrahedron Lett. 2011; 52: 1934
- 11 Awata A, Arai T. Chem. Eur. J. 2012; 18: 8278
- 12a Pesciaioli F, Righi P, Mazzanti A, Bartoli G, Bencivenni G. Chem. Eur. J. 2011; 17: 2842
- 12b Dou X, Lu Y. Chem. Eur. J. 2012; 18: 8315
- 12c Noole A, Sucman NS, Kabeshov MA, Kanger T, Macaev FZ, Malkov AV. Chem. Eur. J. 2012; 18: 14929
- 12d Palumbo C, Mazzeo G, Mazziotta A, Gambacorta A, Loreto MA, Migliorini A, Superchi S, Tofani D, Gasperi T. Org. Lett. 2011; 13: 6248
- 13a Meyers C, Carreira EM. Angew. Chem. Int. Ed. 2003; 42: 694 ; Angew. Chem. 2003, 115, 718
- 13b Marti C, Carreira EM. J. Am. Chem. Soc. 2005; 127: 11505
- 14a Fritschi H, Leutenegger U, Pfaltz A. Helv. Chim. Acta 1988; 71: 1553
- 14b Lowenthal RE, Abiko A, Masamune S. Tetrahedron Lett. 1990; 31: 6005
- 14c Evans DA, Woerpel KA, Hinman MM, Faul MM. J. Am. Chem. Soc. 1991; 113: 726
- 14d Leutenegger U, Umbricht G, Fahrni C, von Matt P, Pfaltz A. Tetrahedron 1992; 48: 2143
- 14e Ito K, Katsuki T. Synlett 1993; 638
- 14f Lo MM.-C, Fu GC. J. Am. Chem. Soc. 1998; 120: 10270
- 15a Nishiyama H, Itoh Y, Matsumoto H, Park S.-B, Itoh K. J. Am. Chem. Soc. 1994; 116: 2223
- 15b Nishiyama H, Itoh Y, Sugawara Y, Matsumoto H, Aoki K, Itoh K. Bull. Chem. Soc. Jpn. 1995; 68: 1247
- 15c Miller JA, Jin W, Nguyen ST. Angew. Chem. Int. Ed. 2002; 41: 2953
- 15d Ito J, Ujiie S, Nishiyama H. Chem. Eur. J. 2010; 16: 4986
- 15e Abu-Elfotoh A.-M, Phomkeona K, Shibatomi K, Iwasa S. Angew. Chem. Int. Ed. 2010; 49: 8439
- 16a Nakamura A, Konishi A, Tatsuno Y, Otsuka S. J. Am. Chem. Soc. 1978; 100: 3443
- 16b Nakamura A, Konishi A, Tsujitani R, Kudo M, Otsuka S. J. Am. Chem. Soc. 1978; 100: 3449
- 16c Niimi T, Uchida T, Irie R, Katsuki T. Adv. Synth. Catal. 2001; 343: 79
- 16d Ikeno T, Sato M, Sekino H, Nishizuka A, Yamada T. Bull. Chem. Soc. Jpn. 2001; 74: 2139
- 16e Ikeno T, Iwakura I, Yamada T. J. Am. Chem. Soc. 2002; 124: 15152
- 16f Chen Y, Ruppel JV, Zhang XP. J. Am. Chem. Soc. 2007; 129: 12074
- 16g Chen Y, Zhang XP. J. Org. Chem. 2007; 72: 5931
- 16h Shitama H, Katsuki T. Chem. Eur. J. 2007; 13: 4849
- 17a Doyle MP, Brandes BD, Kazala AP, Pieters RJ, Jarstfer MB, Watkins LM, Eagle CT. Tetrahedron Lett. 1990; 31: 6613
- 17b Doyle MP, Winchester WR, Hoorn JA. A, Lynch V, Simonsen SH, Ghosh R. J. Am. Chem. Soc. 1993; 115: 9968
- 17c Doyle MP, Austin RE, Bailey AS, Dwyer MP, Dyatkin AB, Kalinin AV, Kwan MM. Y, Liras S, Oalmann CJ, Pieters RJ, Protopopova MN, Raab CE, Roos GH. P, Zhou Q.-L, Martin SF. J. Am. Chem. Soc. 1995; 117: 5763
- 17d Lou Y, Horikawa M, Kloster RA, Hawryluk NA, Corey EJ. J. Am. Chem. Soc. 2004; 126: 8916 ; see also ref. 21
- 18a Doyle MP, Zhou Q.-L, Charnsangavej C, Longoria MA, McKervey MA, García CF. Tetrahedron Lett. 1996; 37: 4129
- 18b Davies HM. L, Bruzinski PR, Fall MJ. Tetrahedron Lett. 1996; 37: 4133
- 18c Davies HM. L, Nagashima T, Klino JL. III. Org. Lett. 2000; 2: 823
- 18d Davies HM. L, Townsend RJ. J. Org. Chem. 2001; 66: 6595
- 18e Davies HM. L, Venkataramani C. Org. Lett. 2003; 5: 1403
- 18f Nowlan DT. III, Gregg TM, Davies HM. L, Singleton DA. J. Am. Chem. Soc. 2003; 125: 15902
- 18g Hedley SJ, Ventura DL, Dominiak PM, Nygren CL, Davies HM. L. J. Org. Chem. 2006; 71: 5349
- 18h Ventura DL, Li Z, Coleman MG, Davies HM. L. Tetrahedron 2009; 65: 3052
- 18i Bonge HT, Kaboli M, Hansen T. Tetrahedron Lett. 2010; 51: 5375
- 19a Watanabe N, Ogawa T, Ohtake Y, Ikegami S, Hashimoto S. Synlett 1996; 85
- 19b Saito H, Oishi H, Kitagaki S, Nakamura S, Anada M, Hashimoto S. Org. Lett. 2002; 4: 3887
- 19c Minami K, Saito H, Tsutsui H, Nambu H, Anada M, Hashimoto S. Adv. Synth. Catal. 2005; 347: 1483
- 19d Tsutsui H, Abe T, Nakamura S, Anada M, Hashimoto S. Chem. Pharm. Bull. 2005; 53: 1366
- 19e Takeda K, Oohara T, Anada M, Nambu H, Hashimoto S. Angew. Chem. Int. Ed. 2010; 49: 6979
- 19f DeAngelis A, Dmitrenko O, Yap GP. A, Fox JM. J. Am. Chem. Soc. 2009; 131: 7230
- 20a Davies HM. L, Bruzinski PR, Lake DH, Kong N, Fall MJ. J. Am. Chem. Soc. 1996; 118: 6897
- 20b Hansen J, Autschbach J, Davies HM. L. J. Org. Chem. 2009; 74: 6555
- 21a Watanabe N, Matsuda H, Kuribayashi H, Hashimoto S. Heterocycles 1996; 42: 537
- 21b Kitagaki S, Matsuda H, Watanabe N, Hashimoto S. Synlett 1997; 1171
- 21c Goto T, Takeda K, Anada M, Ando K, Hashimoto S. Tetrahedron Lett. 2011; 52: 4200 ; and references cited therein
- 22a Doyle MP, Griffin JH, Bagheri V, Dorow RL. Organometallics 1984; 3: 53
- 22b Doyle MP, Bagheri V, Wandless TJ, Harn NK, Brinker DA, Eagle CT, Loh K.-L. J. Am. Chem. Soc. 1990; 112: 1906
- 22c O’Bannon PE, Dailey WP. Tetrahedron 1990; 46: 7341
For reviews, see:
The total synthesis of welwitindolinone A isonitrile, see:
Example of racemic synthesis of spiro-cyclopropane oxindoles, see:
Example of racemic synthesis of spiro-epoxyoxindoles, see:
For the catalytic asymmetric symthesis of spiro epoxyoxindole, see:
For examples of Cu(I)-catalyzed enantioselective cyclopropanation, see:
For examples of Ru(II)-catalyzed enantioselective cyclopropanation, see:
For examples of Co(II)-catalyzed enantioselective cyclopropanation, see:
For examples of Rh(II)-catalyzed enantioselective cyclopropanation, see:
For selected examples of catalytic asymmetric cyclopropantion with aryl diazoacetates, see: