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-00000084.xml
Synthesis 2015; 47(01): 134-140
DOI: 10.1055/s-0034-1379043
DOI: 10.1055/s-0034-1379043
paper
Palladium-Catalyzed Asymmetric Allylic Alkylation Reaction of 2-Monosubstituted Indolin-3-ones
Further Information
Publication History
Received: 16 July 2014
Accepted after revision: 08 August 2014
Publication Date:
29 September 2014 (online)
![](https://www.thieme-connect.de/media/synthesis/201501/lookinside/thumbnails/10.1055-s-0034-1379043-1.jpg)
Abstract
An efficient and practical method was developed for the synthesis of 2,2-disubstituted indolin-3-ones by palladium-catalyzed asymmetric allylic alkylation. Enantioselective construction of quaternary carbon centers was also realized in this way.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
-
References
- 1a Steyn PS. Tetrahedron Lett. 1971; 3331
- 1b Steyn PS. Tetrahedron 1973; 29: 107
- 1c Hutchison AJ, Kishi Y. J. Am. Chem. Soc. 1979; 101: 6786
- 2a Birch AJ, Wright JJ. J. Chem. Soc., Chem. Commun. 1969; 644
- 2b Birch AJ, Wright JJ. Tetrahedron 1970; 26: 2329
- 2c Birch AJ, Russell RA. Tetrahedron 1972; 28: 2999
- 2d Williams RM, Glinka T, Kwast E, Coffman H, Stille JK. J. Am. Chem. Soc. 1990; 112: 808
- 3a Bhakuni DS, Silva M, Matlin SA, Sammes PG. Phytochemistry 1976; 15: 574
- 3b Stoermer D, Heathcock CH. J. Org. Chem. 1993; 58: 564
- 4a Liu J.-F, Jiang Z.-Y, Wang R.-R, Zeng Y.-T, Chen J.-J, Zhang X.-M, Ma Y.-B. Org. Lett. 2007; 9: 4127
- 4b Karadeolian A, Kerr MA. Angew. Chem. Int. Ed. 2010; 49: 1133
- 4c Karadeolian A, Kerr MA. J. Org. Chem. 2010; 75: 6830
- 4d Lee J, Panek JS. Org. Lett. 2011; 13: 502
- 4e Zhang X, Mu T, Zhan FX, Ma LJ, Liang GX. Angew. Chem. Int. Ed. 2011; 50: 6164
- 5a Blackman AJ, Hambly TW, Picker K, Taylor WC, Thirasasana N. Tetrahedron Lett. 1987; 28: 5561
- 5b Liu Y, McWhorter WW. J. Am. Chem. Soc. 2003; 125: 4240
- 5c Higuchi K, Sato Y, Tsuchimochi M, Sugiura K, Hatori M, Kawasaki T. Org. Lett. 2009; 11: 197
- 6a Takahashi I, Takahashi K, Ichimura M, Morimoto M, Asano K, Kawamoto I, Tomita F, Nakano H. J. Antibiot. 1988; 41: 1915
- 6b Fukuda Y, Nakatani K, Ito Y, Terashima S. Tetrahedron Lett. 1990; 31: 6699
- 7a Lednicer D, Emmert DE. J. Heterocycl. Chem. 1970; 7: 575
- 7b Zhang X, Foote CS. J. Am. Chem. Soc. 1993; 115: 8867
- 7c Tommasi G, Bruni P, Greci L, Sgarabotto P, Righi L. J. Chem. Soc., Perkin Trans. 1 1999; 681
- 7d Liu Y, McWhorter WW. Jr. J. Org. Chem. 2003; 68: 2618
- 7e Boger DL, Nishi T. Bioorg. J. Med. Chem. 1995; 3: 67
- 7f Yun S, Kim K. J. Chem. Soc., Perkin Trans. 1 2002; 2360
- 7g Buller MJ, Cook TG, Kobayashi Y. Heterocycles 2007; 72: 163
- 7h Gowan M, Caille AS, Lau CK. Synlett 1997; 1312
- 7i Merour J.-Y, Chichereau L, Desarbre E, Gadonneix P. Synthesis 1996; 519
- 7j Kamel AA, Abdou WM. Synlett 2007; 1269
-
7k Yamada K, Kur-okawa T, Tokuyama H, Fukuyama T. J. Am. Chem. Soc. 2003; 125: 6630
- 7l Astolfi P, Bruni P, Greci L, Stipa P, Righi L, Rizzoli C. Eur. J. Org. Chem. 2003; 2626
- 7m Li L, Han M, Xiao M, Xie Z. Synlett 2011; 1727
- 7n Rueping M, Raja S, Nuñez A. Adv. Synth. Catal. 2011; 353: 563
- 7o Parra A, Alfaro R, Marzo L, Moreno-Carrasco A, Garcia Ruano JL, Aleman J. Chem. Commun. 2012; 48: 9759
- 7p Rueping M, Rasappan R, Raja S. Helv. Chim. Acta 2012; 95: 2296
- 7q Liu J.-X, Zhou Q.-Q, Deng J.-G, Chen Y.-C. Org. Biomol. Chem. 2013; 11: 8175
- 7r Rueping M, Raja S. Beilstein J. Org. Chem. 2012; 8: 1819
- 7s Yin Q, You S.-L. Chem. Sci. 2011; 3: 1344
- 7t Higuchi K, Masuda K, Koseki T, Hatori M, Sakamoto M, Kawasaki T. Heterocycles 2007; 73: 641
-
8a Trost BM, Van Vranken DL. Chem. Rev. 1996; 96: 395
- 8b Pfaltz A, Lautens M In Comprehensive Asymmetric Catalysis . Vol. 2. Jacobsen EN, Pfaltz A, Yamamoto H. Springer; New York: 1999: 833
-
8c Trost BM, Crawley ML. Chem. Rev. 2003; 103: 2921
- 8d Lu Z, Ma S. Angew. Chem. Int. Ed. 2008; 47: 258
- 8e Ding C.-H, Hou X.-L. Top. Organomet. Chem. 2011; 36: 247
-
9a Genet JP, Ferroud D, Juge S, Monte JR. Tetrahedron Lett. 1986; 27: 4573
- 9b Nakoji M, Kanayama T, Okino T, Takemoto Y. Org. Lett. 2001; 3: 3329
- 9c Kuwano R, Ito Y. J. Am. Chem. Soc. 1999; 121: 3236
- 9d Kuwano R, Nishio R, Ito Y. Org. Lett. 1999; 1: 837
- 9e Wang Y. Ph.D. Dissertation. Shanghai Institute of Organic Chemistry; P. R. of China: 2002
- 9f Maity P, König B. Synthesis 2006; 2719
- 9g Nemoto T, Harada T, Matsumoto T, Hamada Y. Tetrahedron Lett. 2007; 48: 6304
- 9h Malinowski JT, McCarver SJ, Johnson JS. Org. Lett. 2012; 14: 2878
- 9i Ogasawara M, Ngo HL, Sakamoto T, Takahashi T, Lin W. Org. Lett. 2005; 7: 2881
- 10a You S.-L, Zhu X.-Z, Luo Y.-M, Hou X.-L, Dai L.-X. J. Am. Chem. Soc. 2001; 123: 7471
- 10b Sun N, Hou X.-L. Org. Lett. 2004; 6: 4399
- 10c Zheng W.-H, Sun N, Hou X.-L. Org. Lett. 2005; 7: 5151
- 10d Zheng W.-H, Zheng B.-H, Zhang Y, Hou X.-L. J. Am. Chem. Soc. 2007; 129: 7718
- 10e Zhang K, Peng Q, Hou X.-L, Wu Y.-D. Angew. Chem. Int. Ed. 2008; 47: 1741
- 10f Chen J.-P, Ding C.-H, Liu W, Hou X.-L, Dai L.-X. J. Am. Chem. Soc. 2010; 132: 15493
- 10g Zheng B.-H, Ding C.-H, Hou X.-L. Synlett 2011; 2262
- 10h Yang X.-F, Ding C.-H, Li X.-H, Huang J.-Q, Hou X.-L, Dai L.-X, Wang P.-J. J. Org. Chem. 2012; 77: 8980
-
10i Li X.-H, Zheng B.-H, Ding C.-H, Hou X.-L. Org. Lett. 2013; 15: 6086
- 11a Fuji K. Chem. Rev. 1993; 93: 2037
- 11b Corey EJ, Guzman-Perez A. Angew. Chem. Int. Ed. 1998; 37: 388
- 11c O’Brien P. J. Chem. Soc., Perkin Trans. 1 2001; 95
- 11d Christoffers J, Mann A. Angew. Chem. Int. Ed. 2001; 40: 4591
- 11e Christoffers J, Baro A. Adv. Synth. Catal. 2005; 347: 1473
- 11f Trost BM, Jiang C. Synthesis 2006; 369
- 11g Bella M, Casperi T. Synthesis 2009; 1583
- 11h Hong AY, Stoltz BM. Eur. J. Org. Chem. 2013; 2745
For racemic versions, see selected examples:
For asymmetric and catalytic versions, see:
For reviews, see:
Reviews: