Palladium-Catalyzed Asymmetric Allylic Alkylation Reaction of 2-Mono­substituted Indolin-3-ones

Tie-Gen Chen; Ping Fang; Xue-Long Hou; Li-Xin Dai

doi:10.1055/s-0034-1379043

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(01): 134-140
DOI: 10.1055/s-0034-1379043

paper

Palladium-Catalyzed Asymmetric Allylic Alkylation Reaction of 2-Monosubstituted Indolin-3-ones

Tie-Gen Chen

^aState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China

,

Ping Fang

^aState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China

,

Xue-Long Hou*

^aState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China

^bShanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China Fax: +86(21)64166128 eMail: xlhou@sioc.ac.cn

,

Li-Xin Dai

^aState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China

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Abstract

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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.

Key words

palladium - allylic substitution - asymmetric catalysis - indolines - quaternary carbon

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Referenzen

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

For racemic versions, see selected examples:

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

For asymmetric and catalytic versions, see:

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

For reviews, see:

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

Reviews:

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

Zusatzmaterial

Supporting Information

Palladium-Catalyzed Asymmetric Allylic Alkylation Reaction of 2-Mono­substituted Indolin-3-ones

Palladium-Catalyzed Asymmetric Allylic Alkylation Reaction of 2-Monosubstituted Indolin-3-ones