Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2014; 25(09): 1246-1252
DOI: 10.1055/s-0033-1341201
DOI: 10.1055/s-0033-1341201
letter
Palladium-Catalyzed Interceptive Decarboxylative Addition of Allyl Carbonates with Carbonyl Group
Further Information
Publication History
Received: 10 February 2014
Accepted after revision: 19 March 2014
Publication Date:
10 April 2014 (online)
Abstract
The first palladium-catalyzed interceptive decarboxylative 1,4-addition of allyl carbonates with squarates is reported. Interestingly, the C-3 carbonyl group of N-substituted isatins undergoes smooth decarboxylative 1,2-addition with allyl carbonates. This transformation offers a straightforward method for the synthesis of spiro-oxepane-fused 2-oxindole.
Key words
palladium - allylation - conjugate addition - allyl complexes - spiro compounds - metathesisSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References and Notes
- 1a Shimizu I, Yamada T, Tsuji J. Tetrahedron Lett. 1980; 21: 3199
-
1b Shimizu I, Tsuji J. J. Am. Chem. Soc. 1982; 104: 5844
-
2 Tsuda T, Chujo Y, Nishi S.-i, Tawara K, Saegusa T. J. Am. Chem. Soc. 1980; 102: 6381
- 4a Weaver JD, Recio A, Grenning AJ, Tunge JA. Chem. Rev. 2011; 111: 1846 ; and references cited therein
- 4b Mohr JT, Behenna DC, Harned AM, Stoltz BM. Angew. Chem. Int. Ed. 2005; 44: 6924
- 4c Trost BM, Xu J, Schmidt T. J. Am. Chem. Soc. 2009; 131: 18343
- 4d Rodriguez N, Manjolinho F, Grunberg MF, Gooben LJ. Chem. Eur. J. 2011; 17: 13688
- 4e Tunge JA, Burger EC. Eur. J. Org. Chem. 2005; 1715
- 4f Behenna DC, Liu Y, Yurino T, Kim J, White DE, Virgil SC, Stoltz BM. Nat. Chem. 2012; 4: 130
- 4g Reeves CM, Eidamshaus C, Kim J, Stoltz BM. Angew. Chem. Int. Ed. 2013; 52: 6718
- 5a Shim J.-G, Nakamura H, Yamamoto Y. J. Org. Chem. 1998; 63: 8470
- 5b Streuff J, White DE, Virgil SC, Stoltz BM. Nat. Chem. 2010; 2: 192
- 5c Wang C, Tunge JA. Org. Lett. 2005; 7: 2137
- 6 Nakamura H, Sekido M, Ito M, Yamamoto Y. J. Am. Chem. Soc. 1998; 120: 6838
- 7 Patil NT, Huo Z, Yamamoto Y. J. Org. Chem. 2006; 71: 6991
- 8a Yeagley AA, Lowder MA, Chruma JJ. Org. Lett. 2009; 11: 4022
- 8b Yeagley AA, Chruma JJ. Org. Lett. 2007; 9: 2879
- 9a Shintani R, Park S, Hayashi T. J. Am. Chem. Soc. 2007; 129: 14866
- 9b Shintani R, Murakami M, Hayashi T. Org. Lett. 2009; 11: 457
- 9c Shintani R, Hayashi S, Murakami M, Takeda M, Hayashi T. Org. Lett. 2009; 11: 3754
- 9d Shintani R, Park S, Shirozu F, Murakami M, Hayashi T. J. Am. Chem. Soc. 2008; 130: 16174
- 9e Park S, Shintani R, Hayashi T. Chem. Lett. 2009; 38: 204
- 9f Shintani R, Murakami M, Hayashi T. J. Am. Chem. Soc. 2007; 129: 12356
- 10 George SC, John J, Anas S, John J, Yamamoto Y, Suresh E, Radhakrishnan KV. Eur. J. Org. Chem. 2010; 5489
- 11 George SC, Thulasi S, Anas S, Radhakrishnan KV, Yamamoto Y. Org. Lett. 2011; 13: 4984
- 12 Yus M, Gomez JC. G, Foubelo F. Chem. Rev. 2013; 113: 5595
-
13a Nakamura H, Iwama H, Yamamoto Y. J. Am. Chem. Soc. 1996; 118: 6641
- 13b Nakamura H, Asao N, Yamamoto Y. J. Chem. Soc., Chem. Commun. 1995; 1273
- 14 Barker TJ, Jarvo ER. Org. Lett. 2009; 11: 1047
- 15a Zhang X, Chen D, Liu X, Feng X. J. Org. Chem. 2007; 72: 5227
- 15b Huddad TD, Hirayama LC, Taynton P, Singaram B. Tetrahedron Lett. 2008; 49: 508
- 16 Johnson AG, Loertscher BM, Moeck AR, Matthews SS, Ess DH, Castle SL. Bioorg. Med. Chem. Lett. 2011; 21: 2706
- 17a Zanoni G, Gladiali S, Marchetti A, Piccinini P, Tredici I, Vidari G. Angew. Chem. Int. Ed. 2004; 43: 846
- 17b Kimura M, Shimizu M, Shibata K, Tazoe M, Tamaru Y. Angew. Chem. 2003; 115: 3514
- 17c Zhu S.-F, Yang Y, Wang L.-X, Zhou Q.-L. Org. Lett. 2005; 7: 2333
- 17d Shen K.-H, Yao C.-F. J. Org. Chem. 2006; 71: 3980
- 17e Yatsumonji Y, Nishimura T, Tsubouchi A, Noguchi K, Takeda T. Chem. Eur. J. 2009; 15: 2680
- 17f Barczak NT, Jarvo ER. Eur. J. Org. Chem. 2008; 5507
- 18 Lou S, Westbrook JA, Schaus SE. J. Am. Chem. Soc. 2004; 126: 11440
- 19a Yamamoto Y, Ohno M, Eguchi S. J. Am. Chem. Soc. 1995; 117: 9653
- 19b Geng F, Liu J, Paquette LA. Org. Lett. 2002; 4: 71
- 19c Varea T, Grancha A, Asenio G. Tetrahedron 1995; 51: 12373
- 19d Liebeskind LS. Tetrahedron 1989; 45: 3053
- 19e Tomooka CS, Liu H, Moore HW. J. Org. Chem. 1996; 61: 6009
- 19f Paquette LA, Geng F. J. Am. Chem. Soc. 2002; 124: 9199
- 19g Namyslo JC, Kaufmann DE. Chem. Rev. 2003; 103: 1485
- 20a Paquette LA. Eur. J. Org. Chem. 1998; 1709
- 20b Paquette LA, Doyon J. J. Org. Chem. 1997; 62: 1723
- 20c Morwick T, Paquette LA. J. Org. Chem. 1996; 61: 146
- 20d Negri JT, Morwick T, Doyon J, Wilson PD, Hickey ER, Paquette LA. J. Am. Chem. Soc. 1993; 115: 12189
- 20e Varea T, Alcalde A, Decastillo CL, de Arellano CR, Cossio FP, Asensio G. J. Org. Chem. 2012; 77: 6327
- 20f Varea T, Alcalde A, Grancha A, Lloret J, Asensio G, Lledos A. J. Org. Chem. 2008; 73: 6521
- 21a Liebeskind LS, Chidambarum R, Mitchell D, Foster BS. Pure Appl. Chem. 1988; 60: 27
- 21b Crispini A, Pucci D, Aiello I, Ghedini M. Inorg. Chim. Acta 2000; 304: 219
- 22 Spectral Data of 3aa Rf = 0.61 (EtOAc–hexane, 3:7). IR (neat): 2961, 2935, 2874, 1778, 1638, 1460, 1331, 1061 cm–1. 1H NMR (500 MHz, CDCl3): δ = 5.98–5.91 (m, 2 H), 5.39–5.15 (m, 4 H), 4.77 (d, J = 5.5 Hz, 2 H), 4.40 (t, J = 6.5 Hz, 2 H), 4.27 (d, J = 5.5 Hz, 2 H), 3.71 (t, J = 6.5 Hz, 2 H), 1.75 (quin, J = 7.0 Hz, 2 H), 1,58 (quin, J = 7.0 Hz, 2 H), 1.47–1.36 (m, 4 H), 0.96 (t, J = 7.5 Hz, 3 H), 0.91 (t, J = 7.5 Hz, 3 H). 13C NMR (125 MHz, CDCl3): δ = 184.9, 167.4, 137.1, 134.3, 132.6, 118.8, 116.8, 108.2, 73.3, 71.2, 66.6, 65.5, 31.9, 31.5, 19.2, 18.7, 13.8, 13.6. ESI-HRMS: m/z calcd for C18H28O5Na [M + Na]+: 347.18344; found: 347.18249.
- 23 See the Supporting Information.
- 24a Cameron AF. B, Hunt JS, Oughton JF, Wilkinson PA, Wilson BM. J. Chem. Soc. 1953; 3864
- 24b Zajac WW, Byrne KJ. J. Org. Chem. 1970; 35: 3375
- 24c Dauben JM, Gerdes WG, Look GC. J. Org. Chem. 1986; 51: 4964
- 25 Singh GS, Desta ZY. Chem. Rev. 2012; 112: 6104 ; and references cited therein
- 26 CCDC-984183.
- 27 Fensome A, Adams WR, Adams AL, Berrodin TJ, Cohen J, Huselton C, Illenberger A, Karen JC, Hudak MA, Marella AG, Melenski EG, McComas CC, Mugford CA, Slayeden OD, Yudt M, Zhang J, Zhang P, Zhu Y, Winneker RC, Wrobel JE. J. Med. Chem. 2008; 51: 1861
- 28 Kumari G, ;Nutan; Modi M, Gupta SK, Singh RK. Eur. J. Med. Chem. 2011; 46: 1181
- 29a Lo MM.-C, Newmann CS, Nagayams S, Perlstein EO, Schreiber SL. J. Am. Chem. Soc. 2005; 127: 10130
- 29b Ding K, Lu Y, Nikolovska-Coleska Z, Qui S, Ding Y, Gao W, Stuckey J, Krajewski K, Roller PP, Tomita Y, Parrish DA, Deschamps JR, Wang S. J. Am. Chem. Soc. 2004; 126: 16077
- 30 Rottmann M, McNamara C, Yeung BK. S, Lee MC. S, Zhou B, Russell B, Seitz P, Plouffe DM, Dharia NV, Tan J, Cohen SB, Spencer KR, Gonzalez-Paez GE, Lakshminarayana SB, Goh A, Suwanarusk R, Jegla T, Schmitt EK, Beck H.-P, Brun R, Nosten F, Renia L, Dartois V, Keller TH, Fidock DA, Winzeler EA, Diagana TT. Science 2010; 329: 1175
- 31 Ding K, Lu Y, Nikolovska-Coleska Z, Wang G, Qiu S, Shangary S, Gao W, Qin D, Stukey J, Krajewski K, Roller PP, Wang S. J. Med. Chem. 2006; 49: 3432