Organocatalytic Asymmetric Synthesis and Use of Organoselenium Compounds

Dedicated to our mentor Professor Marcello Tiecco

Abstract

In the last ten years organocatalysis has emerged as an efficient and sustainable strategy for the asymmetric synthesis of chiral molecules. Optically active intermediates for novel interesting transformations are generated under mild and operationally simple conditions when selenium-containing compounds are used as reaction partners. The peculiar reactivity of organoselenium compounds has been exploited in practical one-pot sequences for the asymmetric construction of densely functionalized compounds starting from simple precursors.

1 Introduction

2 Organocatalytic Asymmetric Synthesis of α-Seleno Carbonyl Compounds and Applications

3 Organocatalytic Additions to Vinyl Selenones for the Enantioselective Construction of Quaternary Stereocenters

4 Concluding Remarks

Key words

selenium - asymmetric catalysis - organocatalysis - ­Michael addition - domino reaction

• References


For books and comprehensive reviews on this area, see:
• 1a Organoselenium Chemistry: Synthesis and Reactions. Wirth T. Wiley-VCH; Weinheim: 2012
• 1b Organoselenium Chemistry – Modern Developments in Organic Synthesis. Wirth T. Springer; Berlin: 2000
• 1c Organoselenium Chemistry – A Practical Approach. Back TG. Oxford University Press; Oxford: 1999
• 1d Soloshonok VA, Nelson DJ. Beilstein J. Org. Chem. 2011; 7: 744
• 1e Freudendahl DM, Shazhad SA, Wirth T. Eur. J. Org. Chem. 2009; 1649
• 2a Godoi M, Paixao MW, Braga AL. Dalton Trans. 2011; 40: 11347
• 2b Freudendahl DM, Santoro S, Shahzad SA, Santi C, Wirth T. Angew. Chem. Int. Ed. 2009; 48: 8409
• 2c Braga AL, Ludtke DS, Vargas F, Braga RC. Synlett 2006; 1453
• 2d Zhu C, Huang Y. Curr. Org. Chem. 2006; 10: 1905
• 2e Wirth T. Angew. Chem. Int. Ed. 2000; 39: 3740
• 3a Tiecco M, Testaferri L, Bagnoli L, Marini F, Santi C, Temperini A, Scarponi G, Sternativo S, Terlizzi R, Tomassini C. ARKIVOC 2006; (vii): 186
• 3b Tiecco M, Testaferri L, Bagnoli L, Scarponi C, Temperini A, Marini F, Santi C. Tetrahedron: Asymmetry 2006; 17: 2768
• 3c Tiecco M, Testaferri L, Bagnoli L, Scarponi C, Purgatorio V, Temperini A, Marini F, Santi C. Tetrahedron: Asymmetry 2005; 16: 2429
• 3d Tiecco M, Testaferri L, Santi C, Tomassini C, Marini F, Bagnoli L, Temperini A. Chem. Eur. J. 2002; 8: 1118
• 3e Tiecco M, Testaferri L, Marini F, Sternativo S, Santi C, Bagnoli L, Temperini A. Tetrahedron: Asymmetry 2001; 12: 3053
• 3f Tiecco M, Testaferri L, Marini F, Sternativo S, Bagnoli L, Santi C, Temperini A. Tetrahedron: Asymmetry 2001; 12: 1493

For recent examples, see:
• 4a Sternativo S, Marini F, Del Verme F, Calandriello A, Testaferri L, Tiecco M. Tetrahedron 2010; 66: 6851
• 4b Tiecco M, Testaferri L, Marini F, Sternativo S, Santi C, Bagnoli L, Temperini A. Tetrahedron 2007; 63: 5482
• 4c Tiecco M, Testaferri L, Bagnoli L, Scarponi C, Temperini A, Marini F, Santi C. Tetrahedron: Asymmetry 2007; 18: 2758
• 4d Tiecco M, Testaferri L, Temperini A, Bagnoli L, Marini F, Santi C. Chem. Eur. J. 2004; 10: 1752
• 4e Tiecco M, Testaferri L, Temperini A, Terlizzi R, Bagnoli L, Marini F, Santi C. Org. Biomol. Chem. 2007; 5: 3510
• 5 Pluim H, Wynberg H. Tetrahedron Lett. 1979; 20: 1251
• 6 Wang J, Li H, Mei Y, Lou B, Xu D, Xie D, Guo H, Wang W. J. Org. Chem. 2005; 70: 5678
• 7a Denmark SE, Kalyani D, Collins WR. J. Am. Chem. Soc. 2010; 132: 15752
• 7b See also: Guan H, Wang H, Huang D, Shi Y. Tetrahedron 2012; 68: 2728
• 8a Tiecco M, Carlone A, Sternativo S, Marini F, Bartoli G, Melchiorre P. Angew. Chem. Int. Ed. 2007; 46: 6882
• 8b One month later, a similar protocol appeared in the literature: Sundén H, Rios R, Córdova A. Tetrahedron Lett. 2007; 48: 7865
• 9a Franzen J, Marigo M, Fielenbach D, Wabnitz T, Kjarsgaard CA, Jørgensen KA. J. Am. Chem. Soc. 2005; 127: 18296
• 9b Mielgo A, Palomo C. Chem. Asian J. 2008; 3: 922
• 9c Guillena G, Ramon DJ. Curr. Org. Chem. 2011; 15: 296
• 10a Costa CE, Clososki GC, Barchesi HB, Zanotto SP, Nascimento MG, Comasseto JV. Tetrahedron: Asymmetry 2004; 15: 3945
• 10b Gruttadauria M, Lo Meo P, Riela S, D’Anna F, Noto R. Tetrahedron: Asymmetry 2006; 17: 2713
• 10c Yang M, Zhu C, Yuan F, Huang Y, Pan Y. Org. Lett. 2005; 7: 1927
• 10d Tiecco M, Testaferri L, Marini F, Sternativo S, Del Verme F, Santi C, Bagnoli L, Temperini A. Tetrahedron 2008; 64: 3337

For recent reports on the synthesis of highly enantioenriched 1,2-selenoamines, see:
• 11a García Ruano JL, Torrente E, Alonso I, Rodriguez M, Martín-Castro AM, Degl’Innocenti A, Frateschi L, Capperucci A. J. Org. Chem. 2012; 77: 1974
• 11b Braga AL, Schneider PH, Paixao MW, Deobald AM, Peppe C, Bottega DP. J. Org. Chem. 2006; 71: 4305
• 11c Ganesh V, Chandrasekaran S. Synthesis 2009; 3267
• 11d Braga AL, Schwab RS, Alberto EE, Salman SM, Vargas J, Arezedo JB. Tetrahedron Lett. 2009; 50: 2309
• 11e Senatore M, Lattanzi A, Santoro S, Santi C, Della Sala G. Org. Biomol. Chem. 2011; 9: 6205
• 11f For biological properties of 1,2-selenoamines, see: de Souza Prestes A, Terra Stefanello S, Salman SM, Martini Pazini A, Schwab RS, Braga AL, de Vargas Barbosa NB, Rocha JB. T. Mol. Cell. Biochem. 2012; 365: 85
• 11g See also: Woznichak MM, Overcast JD, Robertson K, Neumann HM, May SW. Arch. Biochem. Biophys. 2000; 379: 314
• 11h See further: May SW, Wang L, Gill-Woznichak MM, Browner RF, Ogonowski AA, Smith JB, Pollock SH. J. Pharm. Exp. Ther. 1997; 283: 470
• 12a Hess LC, Posner GH. Org. Lett. 2010; 12: 2120
• 12b For the formation of γ-hydroxy-α,β-unsaturated sulfones and esters starting from enantioenriched α-seleno aldehydes, see: Petersen KS, Posner GH. Org Lett. 2008; 10: 4685
• 13 Armstrong A, Emmerson DP. G. Org. Lett. 2011; 13: 1040
• 14 Genna DT, Hencken CP, Siegler MA, Posner GH. Org. Lett. 2010; 12: 4694
• 15 Giacalone F, Gruttadauria M, Agrigento P, Campisciano V, Noto R. Catal. Commun. 2011; 16: 75
• 16 Marcos V, Aleman J, Garcia Ruano JL, Marini F, Tiecco M. Org. Lett. 2011; 13: 3052

For recent reviews on the organocatalytic enantioselective formation of quaternary stereogenic centers, see:
• 17a Jautze S, Peters R. Synthesis 2010; 365
• 17b Bella M, Gasperi T. Synthesis 2009; 1583
• 18 Marini F, Sternativo S, Del Verme F, Testaferri L, Tiecco M. Adv. Synth. Catal. 2009; 351: 103
• 19 Marini F, Sternativo S, Del Verme F, Testaferri L, Tiecco M. Adv. Synth. Catal. 2009; 351: 1801
• 20 Sternativo S, Calandriello A, Costantino F, Testaferri L, Tiecco M, Marini F. Angew. Chem. Int. Ed. 2011; 50: 9382
• 21 Zhang T, Cheng L, Hameed S, Liu L, Wang D, Chen Y.-J. Chem. Commun. 2011; 47: 6644
• 22 Nielsen M, Jacobsen CB, Holub N, Paixao MW. Jørgensen K. A. Angew. Chem. Int. Ed. 2010; 49: 2668
• 23a Bell M, Poulsen TB, Jørgensen KA. J. Org. Chem. 2007; 72: 3053
• 23b Poulsen TB, Bernardi L, Bell M, Jørgensen KA. Angew. Chem. Int. Ed. 2006; 45: 6551

For recent examples, see:
• 24a Rios R, Sunden H, Vesely J, Zhao G, Dziedzic LP, Cordova A. Adv. Synth. Catal. 2007; 349: 1028
• 24b Hartikka A, Slosarczyk AT, Arvidsson PI. Tetrahedron: Asymmetry 2007; 18: 1403
• 24c Hansen HM, Longbottom DA, Ley SV. Chem. Commun. 2006; 4838
• 24d Wascholowski V, Hansen HM, Longbottom DA, Ley SV. Synthesis 2008; 1269
• 24e Ibrahem I, Zhao GL, Rios R, Vesely J, Sunden H, Dziedzic P, Cordova A. Chem. Eur. J. 2008; 14: 7867
• 24f Lv J, Zhang J, Lin Z, Wang Y. Chem. Eur. J. 2009; 15: 972
• 24g Xuan Y, Nie S, Dong L, Zhang J, Yan M. Org. Lett. 2009; 11: 158
• 24h Del Fiandra C, Piras L, Fini F, Disetti P, Moccia M, Adamo MF. A. Chem. Commun. 2012; 48: 3863
• 25 Miller LC, Sarpong R. Chem. Soc. Rev. 2011; 40: 4550