Synthesis 2015; 47(10): 1357-1378
DOI: 10.1055/s-0034-1378692
review
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in the N-Heterocyclic Carbene (NHC)-Organocatalyzed Stetter Reaction and Related Chemistry

Santhivardhana Reddy Yetra
Organic Chemistry Division, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune – 411008, India   Email: at.biju@ncl.res.in
,
Atanu Patra
Organic Chemistry Division, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune – 411008, India   Email: at.biju@ncl.res.in
,
Akkattu T. Biju*
Organic Chemistry Division, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune – 411008, India   Email: at.biju@ncl.res.in
› Author Affiliations
Further Information

Publication History

Received: 06 January 2015

Accepted after revision: 02 February 2015

Publication Date:
09 April 2015 (eFirst)

Abstract

Recent developments in the N-heterocyclic carbene (NHC)-catalyzed umpolung of aldehydes followed by their interception with activated carbon–carbon double bonds, namely the Stetter reaction, are presented. Advances in the inter- and intramolecular versions of this reaction, enantioselective transformations as well as the use of unactivated olefins in this type of reaction are discussed.

1 Introduction

2 Proposed Mechanism of the Stetter Reaction

3 Intramolecular Stetter Reactions

4 Intermolecular Stetter Reactions

5 Hydroacylation Reactions

6 Applications in Total Synthesis

7 Conclusion

 
  • References

    • 1a Stetter H. Angew. Chem., Int. Ed. Engl. 1976; 15: 639
    • 1b Stetter H, Kuhlmann H In Organic Reactions . Vol. 40. Paquette LA. Wiley & Sons; New York: 1991: 407

      For recent reviews on NHC-organocatalysis, see:
    • 2a Hopkinson MN, Richter C, Schedler M, Glorius F. Nature 2014; 510: 485
    • 2b Mahatthananchai J, Bode JW. Acc. Chem. Res. 2014; 47: 696
    • 2c Ryan SJ, Candish L, Lupton DW. Chem. Soc. Rev. 2013; 42: 4906
    • 2d De Sarkar S, Biswas A, Samanta RC, Studer A. Chem. Eur. J. 2013; 19: 4664
    • 2e Knappke CE. I, Imami A, von Wangelin AJ. ChemCatChem 2012; 4: 937
    • 2f Grossmann A, Enders D. Angew. Chem. Int. Ed. 2012; 51: 314
    • 2g Bugaut X, Glorius F. Chem. Soc. Rev. 2012; 41: 351
    • 2h Hirano K, Piel I, Glorius F. Chem. Lett. 2011; 40: 786
    • 2i Nair V, Menon RS, Biju AT, Sinu CR, Paul RR, Jose A, Sreekumar V. Chem. Soc. Rev. 2011; 40: 5336
    • 2j Izquierdo J, Hutson GE, Cohen DT, Scheidt KA. Angew. Chem. Int. Ed. 2012; 51: 11686
    • 2k Cohen DT, Scheidt KA. Chem. Sci. 2012; 3: 53
    • 2l Vora HU, Wheeler P, Rovis T. Adv. Synth. Catal. 2012; 354: 1617
    • 2m Chiang P.-C, Bode JW In N-Heterocyclic Carbenes . The Royal Society of Chemistry; London: 2011: 399
    • 2n Nair V, Vellalath S, Babu BP. Chem. Soc. Rev. 2008; 37: 2691
    • 2o Enders D, Niemeier O, Henseler A. Chem. Rev. 2007; 107: 5606

      For reviews on the Stetter reaction, see:
    • 3a Read de Alaniz J, Rovis T. Synlett 2009; 1189
    • 3b Rovis T. Chem. Lett. 2008; 37: 2

    • For a recent highlight, see:
    • 3c Christmann M. Angew. Chem. Int. Ed. 2005; 44: 2632

    • See also:
    • 3d Read de Alaniz J, Kerr MS, Moore JL, Rovis R. J. Org. Chem. 2008; 73: 2033
  • 5 Stetter H, Schreckenberg M. Angew. Chem., Int. Ed. Engl. 1973; 12: 81
    • 6a Wanzlick H.-W. Angew. Chem., Int. Ed. Engl. 1962; 1: 75
    • 6b Arduengo AJ. III, Harlow RL, Kline M. J. Am. Chem. Soc. 1991; 113: 361
    • 7a Breslow R. J. Am. Chem. Soc. 1958; 80: 3719
    • 7b Breslow R, Kim R. Tetrahedron Lett. 1994; 35: 699
    • 7c White M, Leeper F. J. Org. Chem. 2001; 66: 5124
    • 8a Nair V, Bindu S, Sreekumar V, Rath NP. Org. Lett. 2003; 5: 665
    • 8b Berkessel A, Elfert S, Yatham VR, Neudörfl J.-M, Schlörer NE, Teles JH. Angew. Chem. Int. Ed. 2012; 51: 12370
    • 8c Berkessel A, Yatham VR, Elfert S, Neudörfl J.-M. Angew. Chem. Int. Ed. 2013; 52: 11158
  • 9 Biju AT, Kuhl N, Glorius F. Acc. Chem. Res. 2011; 44: 1182
  • 10 Moore JL, Silvestri AP, Read de Alaniz J, DiRocco DA, Rovis T. Org. Lett. 2011; 13: 1742
  • 11 Read de Alaniz J, Rovis T. J. Am. Chem. Soc. 2005; 127: 6284
  • 12 Hawkes KJ, Yates BF. Eur. J. Org. Chem. 2008; 5563
  • 13 Ciganek E. Synthesis 1995; 1311
  • 14 Enders D, Breuer K, Runsink J, Teles JH. Helv. Chim. Acta 1996; 79: 1899
  • 15 Kerr MS, Read de Alaniz J, Rovis T. J. Am. Chem. Soc. 2002; 124: 10298
    • 16a Kerr MS, Rovis T. J. Am. Chem. Soc. 2004; 126: 8876
    • 16b Kerr MS, Read de Alaniz J, Rovis T. J. Org. Chem. 2005; 70: 5725
    • 16c Moore JL, Kerr MS, Rovis T. Tetrahedron 2006; 62: 11477
    • 16d Cullen SC, Rovis T. Org. Lett. 2008; 10: 3141
  • 17 Pesch J, Harms K, Bach T. Eur. J. Org. Chem. 2004; 2025
  • 18 Mennen SM, Blank JT, Tran-Dubé MB, Imbriglio JE, Miller SJ. Chem. Commun. 2005; 195
  • 19 Jia M.-Q, Li Y, Rong Z.-Q, You S.-L. Org. Biomol. Chem. 2011; 9: 2072
  • 20 Rong Z.-Q, Li Y, Yang G.-Q, You S.-L. Synlett 2011; 1033
  • 21 Bao Y, Kumagai N, Shibasaki M. Tetrahedron: Asymmetry 2014; 25: 1401
  • 22 Rafiński Z, Kozakiewicz A, Rafinska K. ACS Catal. 2014; 4: 1404
  • 23 Lu T, Gu L, Kang Q, Zhang Y. Tetrahedron Lett. 2012; 53: 6602
  • 24 Collett CJ, Massey RS, Maguire OR, Batsanov AS, O’Donoghue AC, Smith AD. Chem. Sci. 2013; 4: 1514
    • 25a Liu Q, Rovis T. J. Am. Chem. Soc. 2006; 128: 2552
    • 25b Liu Q, Rovis T. Org. Process Res. Dev. 2007; 11: 598
    • 26a Jia M.-Q, You S.-L. Chem. Commun. 2012; 48: 6363
    • 26b Jia M.-Q, Liu C, You S.-L. J. Org. Chem. 2012; 77: 10996
  • 27 Jia M.-Q, You S.-L. Synlett 2013; 24: 1201
  • 28 Filloux CM, Lathrop SP, Rovis T. Proc. Natl. Acad. Sci. 2010; 107: 20666
  • 29 Orellana A, Rovis T. Chem. Commun. 2008; 730
  • 30 Lathrop S, Rovis T. Chem. Sci. 2013; 4: 1668
    • 31a Tiebes J. Diploma Thesis. RWTH Aachen; Germany: 1990
    • 31b Enders D In Stereoselective Synthesis . Springer-Verlag; Heidelberg: 1993: 63
    • 31c Enders D, Bockstiegel B, Dyker H, Jegelka U, Kipphardt H, Kownatka D, Kuhlmann H, Mannes D, Tiebes J, Papadopoulos K In Dechema-Monographies . Vol. 129. VCH; Weinheim: 1993: 209
    • 32a Enders D, Han J, Henseler A. Chem. Commun. 2008; 3989
    • 32b Enders D, Han J. Synthesis 2008; 3864
  • 33 Liu Q, Perreault S, Rovis T. J. Am. Chem. Soc. 2008; 130: 14066
  • 34 Liu Q, Rovis T. Org. Lett. 2009; 11: 2856
    • 35a Steward KM, Gentry EC, Johnson JS. J. Am. Chem. Soc. 2012; 134: 7329
    • 35b Steward KM, Corbett MT, Goodman CG, Johnson JS. J. Am. Chem. Soc. 2012; 134: 20197
  • 36 DiRocco DA, Oberg KM, Dalton DM, Rovis T. J. Am. Chem. Soc. 2009; 131: 10872
  • 37 Um JM, Dirocco DA, Noey EL, Rovis T, Houk KN. J. Am. Chem. Soc. 2011; 133: 11249
  • 38 DiRocco DA, Rovis T. J. Am. Chem. Soc. 2011; 133: 10402
  • 39 DiRocco DA, Noey EL, Houk KN, Rovis T. Angew. Chem. Int. Ed. 2012; 51: 2391
  • 40 Vedachalam S, Tan SM, Teo HP, Cai S, Liu X.-W. Org. Lett. 2012; 14: 174
  • 41 Jousseaume T, Wurz NE, Glorius F. Angew. Chem. Int. Ed. 2011; 50: 1410
  • 42 Kuniyil R, Sunoj RB. Org. Lett. 2013; 15: 5040
  • 43 Sánchez-Larios E, Thai K, Bilodeau F, Gravel M. Org. Lett. 2011; 13: 4942
  • 44 Fang X, Chen X, Lv H, Chi YR. Angew. Chem. Int. Ed. 2011; 50: 11782
  • 45 Fang X, Chen X, Chi YR. Org. Lett. 2011; 13: 4708
  • 46 Wurz NE, Daniliuc CG, Glorius F. Chem. Eur. J. 2012; 18: 16297
  • 47 Stetter H, Bender H.-J. Angew. Chem., Int. Ed. Engl. 1978; 17: 131
  • 48 Bhunia A, Yetra SR, Bhojgude SS, Biju AT. Org. Lett. 2012; 14: 2830
  • 49 Patra A, Bhunia A, Biju AT. Org. Lett. 2014; 16: 4798
  • 50 Kim SM, Jin MY, Kim MJ, Cui Y, Kim YS, Zhang L, Song CE, Ryu DH, Yang JW. Org. Biomol. Chem. 2011; 9: 2069
  • 51 Bortolini O, Fantin G, Fogagnolo M, Giovannini PP, Massi A, Pacifico S. Org. Biomol. Chem. 2011; 9: 8437
  • 52 Bortolini O, Cavazzini A, Dambruoso P, Giovannini PP, Caciolli L, Massi A, Pacificoa S, Ragno D. Green Chem. 2013; 15: 2981
  • 53 Takaki K, Ohno A, Hino M, Shitaoka T, Komeyama K, Yoshida H. Chem. Commun. 2014; 50: 12285
  • 54 Zhang J, Xing C, Tiwari B, Chi YR. J. Am. Chem. Soc. 2013; 135: 8113
    • 55a Wilde MM. D, Gravel M. Angew. Chem. Int. Ed. 2013; 52: 12651
    • 55b For a highlight on this work, see: Connon SJ. Angew. Chem. Int. Ed. 2014; 53: 1203
    • 56a Dresen C, Richter M, Pohl M, Ludeke S, Muller M. Angew. Chem. Int. Ed. 2010; 49: 6600
    • 56b Beigia C, Waltzera S, Zareib M, Müller M. J. Biotechnol. 2014; 191: 64
    • 57a Sanchez-Larios E, Gravel M. J. Org. Chem. 2009; 74: 7536
    • 57b For a related NHC-catalyzed Stetter–aldol–Michael and Stetter–aldol–aldol sequence for the synthesis of bis-indanes see: Sanchez-Larios E, Holmes JM, Daschner CL, Gravel M. Org. Lett. 2010; 12: 5772
  • 58 Sun F.-G, Huang X.-L, Ye S. J. Org. Chem. 2010; 75: 273
  • 59 Sun F.-G, Ye S. Synlett 2011; 1005
  • 60 Hong B.-C, Dange NS, Hsu C.-S, Liao J.-H. Org. Lett. 2010; 12: 4812
  • 61 Hong BC, Dange NS, Hsu C.-S, Liao J.-H, Lee G.-H. Org. Lett. 2011; 13: 1338

    • For initial reports, see:
    • 62a Katada A, Ichioka K, Takagi K, Suzuki M. Org. Lett. 2011; 13: 3722
    • 62b Biju AT, Padmanaban M, Wurz NE, Glorius F. Angew. Chem. Int. Ed. 2011; 50: 8412
  • 63 Willis MC. Chem. Rev. 2010; 110: 725
  • 64 He J, Tang S, Liu J, Su Y, Pan X, She X. Tetrahedron 2008; 64: 8797
  • 65 Hirano K, Biju AT, Piel I, Glorius F. J. Am. Chem. Soc. 2009; 131: 14190
  • 66 Piel I, Steinmetz M, Hirano K, Fröhlich R, Grimme S, Glorius F. Angew. Chem. Int. Ed. 2011; 50: 4983
  • 67 Domingo LR, Saéz JA, Arnó M. RSC Adv. 2012; 2: 7127
  • 68 Bugaut X, Liu F, Glorius F. J. Am. Chem. Soc. 2011; 133: 8130
  • 69 Ajitha MJ, Suresh CH. Tetrahedron Lett. 2013; 54: 7144
    • 70a Liu F, Bugaut X, Schedler M, Fröhlich R, Glorius F. Angew. Chem. Int. Ed. 2011; 50: 12626
    • 70b Schedler M, Fröhlich R, Daniliuc C.-G, Glorius F. Eur. J. Org. Chem. 2012; 4164
  • 71 Schedler M, Wang DS, Glorius F. Angew. Chem. Int. Ed. 2013; 52: 2585
    • 72a Law KR, McErlean CS. P. Chem. Eur. J. 2013; 19: 15852
    • 72b For a related vinylogous Stetter reaction in a cascade process, see: Dell’Amico L, Rassu G, Zambrano V, Sartori A, Curti C, Battistini L, Pelosi G, Casiraghi G, Zanardi F. J. Am. Chem. Soc. 2014; 136: 11107
  • 73 Zhao M, Yang H, Li MM, Chen J, Zhou L. Org. Lett. 2014; 16: 2904
  • 74 Alcaide B, Almendros P, Fernández I, Martínez del Campo T, Naranjo T. Chem. Eur. J. 2015; 21: 1533
  • 75 Lu H, Lin J.-B, Liu J.-B, Xu P.-F. Chem. Eur. J. 2014; 20: 11659
  • 76 Biju AT, Wurz NE, Glorius F. J. Am. Chem. Soc. 2010; 132: 5970
  • 77 Wang Z, Yu Z, Wang Y, She D. Synthesis 2012; 1559
  • 78 Padmanaban M, Biju AT, Glorius F. Org. Lett. 2011; 13: 5624
  • 79 Franz JF, Fuchs PJ. W, Zeitler K. Tetrahedron Lett. 2011; 52: 6952
  • 80 Biju AT, Glorius F. Angew. Chem. Int. Ed. 2010; 49: 9761
    • 81a Dubrovskiy AV, Markina NA, Larock RC. Org. Biomol. Chem. 2013; 11: 191
    • 81b Wu C, Shi F. Asian J. Org. Chem. 2013; 2: 116
    • 81c Tadross PM, Stoltz BM. Chem. Rev. 2012; 112: 3550
    • 81d Gampe CM, Carreira EM. Angew. Chem. Int. Ed. 2012; 51: 3766
    • 81e Bhunia A, Yetra SR, Biju AT. Chem. Soc. Rev. 2012; 41: 3140
    • 81f Okuma K. Heterocycles 2012; 85: 515
  • 82 Vedachalam S, Wong Q.-L, Maji B, Zeng J, Ma J, Liu X.-W. Adv. Synth. Catal. 2011; 353: 219
  • 83 Vedachalam S, Zeng J, Gorityala BK, Antonio M, Liu X.-W. Org. Lett. 2010; 12: 352
  • 84 For a recent review on application of NHC catalysis on natural products synthesis, see reference 2j.
  • 85 Stetter H, Kuhlmann H. Synthesis 1975; 379
  • 86 Trost BM, Shuey CD, Dininno F, Mcelvain SS. J. Am. Chem. Soc. 1979; 101: 1284
  • 87 Baumann KL, Butler DE, Deering CF, Mennen KE, Millar A, Nanninga TN, Palmer CW, Roth BD. Tetrahedron Lett. 1992; 33: 2283
    • 88a Harrington PE, Tius MA. Org. Lett. 1999; 1: 649
    • 88b Harrington PE, Tius MA. J. Am. Chem. Soc. 2001; 123: 8509
  • 89 Galopin CC. Tetrahedron Lett. 2001; 42: 5589
  • 90 Randl S, Blechert S. J. Org. Chem. 2003; 68: 8879
  • 91 Anjaiah S, Chandrasekhar S, Grée R. Adv. Synth. Catal. 2004; 346: 1329
    • 92a Nicolaou KC, Tang YF, Wang JH. Chem. Commun. 2007; 1922
    • 92b Nicolaou KC, Li A, Edmonds DJ. Angew. Chem. Int. Ed. 2006; 45: 7086
  • 93 Xu J, Caro-Diaz EJ. E, Theodorakis EA. Org. Lett. 2010; 12: 3708
  • 94 Sommerwerk S, Kern S, Heller L, Csuk R. Tetrahedron Lett. 2014; 55: 6243