Synthesis 2020; 52(08): 1147-1180
DOI: 10.1055/s-0039-1690817
review
© Georg Thieme Verlag Stuttgart · New York

Internal Chelation within Functionalized Organoindium Reagents: Prospects for Regio- and Stereocontrol in the Allylation, Propargylation and Allenylation of Carbonyl Compounds

Bartosz K. Zambroń
This work was supported by Narodowe Centrum Nauki (National Science Centre) (Grant No. SONATA UMO-2015/19/D/ST5/00713).
Further Information

Publication History

Received: 10 December 2019

Accepted after revision: 19 January 2020

Publication Date:
17 February 2020 (online)


Abstract

The low basicity, selective nucleophilicity, and mildness of organoindium compounds allow for the incorporation of many important yet sensitive functional groups into their structure, including examples capable of intramolecularly chelating the indium center within these reagents. The specific nature of such chelated organoindiums causes the reactions involving them to proceed in a unique manner, often with regio- and stereoselectivity inaccessible with simple organometallic reagents. This review covers the rare examples of regio- and stereoselective allylation, propargylation, and allenylation of carbonyl compounds with chelated organoindiums, including brief descriptions of the applications of the resulting adducts in the asymmetric synthesis of natural products and synthetic targets of biological and medicinal interest.

1 Introduction

2 Internal Chelation Control in the Allylation Processes

2.1 Allylindiums with a Chelating Center at the γ-Position

2.2 Allylindiums with a chelating Center at the δ-Position

2.3 Allylindiums with a Chelating Center at ε- and ζ-Positions

2.4 Allylindiums with a Chelating Center at γ′- and δ′-Positions

3 Internal Chelation Control in Propargylation and Allenylation Processes­

3.1 Additions of Chelated Allenylindiums

3.2 Additions of Chelated Propargylindiums

4 Conclusion

 
  • References

  • 1 Araki S, Ito H, Butsugan Y. J. Org. Chem. 1988; 53: 1831
  • 2 Li CJ, Chan TH. Tetrahedron Lett. 1991; 32: 7017

    • For selected reviews, see:
    • 3a Marshall JA. Chem. Rev. 2000; 100: 3163
    • 3b Podlech J, Maier TC. Synthesis 2003; 633
    • 3c Zanoni G, Pontiroli A, Marchetti A, Vidari G. Eur. J. Org. Chem. 2007; 3599
    • 3d Kargbo RB, Cook GR. Curr. Org. Chem. 2007; 11: 1287
    • 3e Roy UK, Roy S. Chem. Rev. 2010; 110: 2472
    • 3f Kim SH, Lee HS, Kim KH, Kim SH, Kim JN. Tetrahedron 2010; 66: 7065
    • 3g Singh A. Synlett 2013; 24: 1457
    • 3h Shen Z.-L, Wang S.-Y, Chok Y.-K, Xu Y.-H, Loh T.-P. Chem. Rev. 2013; 113: 271
    • 3i Kumar D, Vemula SR, Balasubramanian N, Cook GR. Acc. Chem. Res. 2016; 49: 2169
  • 4 Marshall JA, Grant CM. J. Org. Chem. 1999; 64: 696
    • 5a Araki S, Kamei T, Hirashita T, Yamamura H, Kawai M. Org. Lett. 2000; 2: 847
    • 5b Araki S, Kameda K, Tanaka J, Hirashita T, Yamamura H, Kawai M. J. Org. Chem. 2001; 66: 7919
    • 5c Araki S, Kambe S, Kameda K, Hirashita T. Synthesis 2003; 751
    • 6a Klimczak UK, Zambroń BK. Chem. Commun. 2015; 51: 6796
    • 6b Plata P, Klimczak U, Zambroń BK. J. Org. Chem. 2018; 83: 14527
    • 6c Domin S, Plata P, Zambroń BK. J. Org. Chem. 2019; 84: 12268
    • 6d Klimczak U, Staszewska-Krajewska O, Zambroń BK. RSC Adv. 2016; 6: 26451
  • 7 Domin S, Kędzierski J, Zambroń BK. Org. Lett. 2019; 21: 3904
    • 8a Lee W, Kim K.-H, Surman MD, Miller MJ. J. Org. Chem. 2003; 68: 139
    • 8b Cesario C, Miller MJ. Org. Lett. 2009; 11: 1293
  • 9 Anwar U, Grigg R, Rasparini M, Savic V, Sridharan V. Chem. Commun. 2000; 645
  • 10 Cooper IR, Grigg R, MacLachlan WS, Sridharan V, Thornton-Pett M. Tetrahedron Lett. 2003; 44: 403
    • 11a Mikami K, Shimizu M. J. Synth. Org. Chem. Jpn. 1993; 51: 21
    • 11b Mikami K, Shimizu M, Zhang H.-C, Maryanoff BE. Tetrahedron 2001; 57: 2917
    • 11c Thomas EJ. Chem. Rec. 2007; 7: 115
    • 11d Jiang H, Albrecht Ł, Jørgensen KA. Chem. Sci. 2013; 4: 2287
  • 12 Marshall JA, Hinkle KW. J. Org. Chem. 1995; 60: 1920
  • 13 Donnelly S, Thomas EJ, Arnott EA. Chem. Commun. 2003; 1460
  • 14 Issac MB, Chan T.-H. Tetrahedron Lett. 1995; 36: 8957
    • 15a Loh T.-P, Tan K.-T, Yang J.-Y, Xiang C.-L. Tetrahedron Lett. 2001; 42: 8701
    • 15b Loh T.-P, Tan K.-T, Hu Q.-Y. Tetrahedron Lett. 2001; 42: 8705
    • 15c Tan K.-T, Chng S.-S, Cheng H.-S, Loh T.-P. J. Am. Chem. Soc. 2003; 125: 2958
  • 16 Norsikian S, Lubineau A. Org. Biomol. Chem. 2005; 3: 4089
    • 17a Araki S, Hirashita T, Shimizu K, Ikeda T, Butsugan Y. Tetrahedron 1996; 52: 2803
    • 17b Araki S, Hirashita T, Shimizu H, Yamamura H, Kawai M, Butsugan Y. Tetrahedron Lett. 1996; 37: 8417
    • 17c Hirashita T, Kamei T, Horie T, Yamamura H, Kawai M, Araki S. J. Org. Chem. 1999; 64: 172
    • 18a Schinz H, Seidel CF. Helv. Chim. Acta 1942; 25: 1572
    • 18b Schinz H, Bourquin JP. Helv. Chim. Acta 1942; 25: 1591
    • 18c Bohlmann F, Zdero C, Faass U. Chem. Ber. 1973; 106: 2904
    • 19a Takemoto Y, Anzai M, Yanada R, Fujii N, Ohno H, Ibuka T. Tetrahedron Lett. 2001; 42: 1725
    • 19b Anzai M, Yanada R, Fujii N, Ohno H, Ibuka T, Takemoto Y. Tetrahedron 2002; 58: 5231
    • 20a Ohno H, Hamaguchi H, Tanaka T. Org. Lett. 2000; 2: 2161
    • 20b Ohno H, Hamaguchi H, Tanaka T. J. Org. Chem. 2001; 66: 1867
  • 21 Xin T, Okamoto S, Sato F. Tetrahedron Lett. 1998; 39: 6927
    • 22a Behnke D, Hamm S, Hennig L, Welzel P. Tetrahedron Lett. 1997; 38: 7059
    • 22b Behnke D, Hennig L, Findeisen M, Welzel P, Müller D, Thormann M, Hofmann H.-J. Tetrahedron 2000; 56: 108
  • 23 Morris DI, Greenberger LM, Bruggemann EP, Cardarelli C, Gottesman MM, Pastan I, Seamon KB. Mol. Pharmacol. 1994; 46: 329
  • 24 Babu SA, Yasuda M, Baba A. J. Org. Chem. 2007; 72: 10264
    • 25a Lombardo M, Girotti R, Morganti S, Trombini C. Org. Lett. 2001; 3: 2981
    • 25b Lombardo M, Morganti S, Trombini C. J. Org. Chem. 2003; 68: 997
    • 25c Lombardo M, Girotti R, Morganti S, Trombini C. Chem. Commun. 2001; 2310
    • 25d Lombardo M, Licciulli S, Trombini C. Pure Appl. Chem. 2004; 76: 657
  • 26 Bottoni A, Lombardo M, Miscione GP, Pujol Algué JB, Trombini C. J. Org. Chem. 2008; 73: 418
  • 27 Lombardo M, Licciulli S, Trombini C. Tetrahedron Lett. 2003; 44: 9147
    • 28a Mizushina Y, Xu X, Asano N, Kasai N, Kato A, Takemura M, Asahara H, Linn S, Sugawara F, Yoshida H, Sakaguchi K. Biochem. Biophys. Res. Commun. 2003; 304: 78
    • 28b Popowycz F, Gerber-Lemaire S, Demange R, Rodriguez-Garcia E, Asenjo AT. C, Robina I, Vogel P. Bioorg. Med. Chem. Lett. 2001; 11: 2489
    • 28c Asano N, Oseki K, Kizu H, Matsui K. J. Med. Chem. 1994; 37: 3701
    • 28d Fleet GW. J, Karpas A, Dwek RA, Fellows LE, Tyms AS, Petursson S, Namgoong SK, Ramsden NG, Smith PW. FEBS Lett. 1988; 237: 128
  • 29 Lombardo M, Gianotti K, Licciulli S, Trombini C. Tetrahedron 2004; 60: 11725
  • 30 Palmelund A, Madsen R. J. Org. Chem. 2005; 70: 8248
  • 31 Stanetty C, Baxendale IR. Eur. J. Org. Chem. 2015; 2718
    • 32a Kosma P. Curr. Org. Chem. 2008; 12: 1021
    • 32b Holst O. FEMS Microbiol. Lett. 2007; 271: 3
  • 33 Draskovits M, Stanetty C, Baxendale IR, Mihovilovic MD. J. Org. Chem. 2018; 83: 2647
  • 34 Lombardo M, Pasi F, Tiberi C, Trombini C. Synthesis 2005; 2609
  • 35 Lombardo M, Pasi F, Trombini C. Eur. J. Org. Chem. 2006; 3061
  • 36 Lombardo M, Capdevila MG, Pasi F, Trombini C. Org. Lett. 2006; 8: 3303
    • 37a Schneiter R. Bioessays 1999; 21: 1004
    • 37b Sharma C, Smith T, Li S, Schroepfer GJ. Jr, Needleman DH. Chem. Phys. Lipids 2000; 104: 1
  • 38 Cossy J, Rasamison C, Pardo DG, Marshall JA. Synlett 2001; 629
  • 39 Hirashita T, Kambe S, Tsuji H, Omori H, Araki S. J. Org. Chem. 2004; 69: 5054
  • 40 Hirashita T, Kambe S, Tsuji H, Araki S. Chem. Commun. 2006; 2595
  • 41 Carey JS, Thomas EJ. Synlett 1992; 585
  • 42 Canac Y, Levoirier E, Lubineau A. J. Org. Chem. 2001; 66: 3206
  • 43 Miyabe H, Yamaoka Y, Naito T, Takemoto Y. J. Org. Chem. 2003; 68: 6745
    • 44a Paquette LA, Isaac MB. Heterocycles 1998; 47: 107
    • 44b Paquette LA, Rothhaar RR, Isaac M, Rogers LM, Rogers RD. J. Org. Chem. 1998; 63: 5463
  • 45 Paquette LA, Rothhaar RR. J. Org. Chem. 1999; 64: 217
    • 46a Loh T.-P, Yin Z, Song H.-Y, Tan K.-L. Tetrahedron Lett. 2003; 44: 911
    • 46b Lee K.-C, Loh T.-P. Chem. Commun. 2006; 40: 4209
  • 47 Márquez F, Llebaria A, Delgado A. Org. Lett. 2000; 2: 547
  • 48 Paquette LA, Bennett GD, Chhatriwalla A, Isaac MB. J. Org. Chem. 1997; 62: 3370
  • 49 Paquette LA, Bennett GD, Isaac MB, Chhatriwalla A. J. Org. Chem. 1998; 63: 1836
  • 50 Fischer M, Schmölzer C, Nowikow C, Schmid W. Eur. J. Org. Chem. 2011; 1645
  • 51 Lin M.-J, Loh T.-P. J. Am. Chem. Soc. 2003; 125: 13042
  • 52 Miao W, Lu W, Chan TH. J. Am. Chem. Soc. 2003; 125: 2412