32.5.3.2 Enol Ethers (Update 2017)

F. Bartels; R. Zimmer; M. Christmann

Abstract

In this chapter, recent methods for the preparation and elaboration of enol ethers are summarized. In addition to updates on classical methods, recently developed metal-catalyzed procedures are presented. The relevance of these methods is also demonstrated in the context of natural product synthesis.

Schlüsselwörter

enol ethers - alkoxyallenes - metathesis - Julia alkenation - Wittig alkenation - Suzuki coupling - heterogeneous catalysis - Diels–Alder cycloaddition - cyclization

• 1 Winternheimer DJ, Shade RE, Merlic CA. Synthesis 2010; 2497

• 2 Decostanzi M, Campagne J.-M, Leclerc E. Org. Biomol. Chem. 2015; 13: 7351

• 3 Trost BM, Masters JT. Chem. Soc. Rev. 2016; 45: 2212

• 4 Schmidt B. J. Mol. Catal. A: Chem. 2006; 254: 53

• 5 Das B, Laxminarayana K, Ravikanth B. J. Mol. Catal. A: Chem. 2007; 271: 131

• 6 Srihari P, Mandal SS, Reddy JSS, Srinivasa Rao R, Yadav JS. Chin. Chem. Lett. 2008; 19: 767

• 7 Rafiee E, Kahrizi M, Joshaghani M. Chin. Chem. Lett. 2012; 23: 1363

• 8 Rafiee E, Eavani S. Catal. Commun. 2012; 25: 64

• 9 Rafiee E, Kahrizi M. S. Afr. J. Chem. 2013; 66: 145

• 10 Li P.-H, Li B.-L, Hu H.-C, Zhao X.-N, Zhang Z.-H. Catal. Commun. 2014; 46: 118

• 11 Curini M, Epifano F, Genovese S. Tetrahedron Lett. 2006; 47: 4697

• 12 Jeanmart S, Taylor JB, Parsons RW, Mathews CJ, Smith SC. Tetrahedron Lett. 2013; 54: 3378

• 13 Blanchard D, Cameron TS, Jha M. Mol. Diversity 2013; 17: 827

• 14 Garnsey MR, Matous JA, Kwiek JJ, Coltart DM. Bioorg. Med. Chem. Lett. 2011; 21: 2406

• 15 Kong HI, Gill MA, Hrdina AH, Crichton JE, Manthorpe JM. J. Fluorine Chem. 2013; 153: 151

• 16 Shioiri T, Aoyama T, Mori S. Org. Synth. 1990; 68: 1

• 17 Shimizu Y, Shi S.-L, Usuda H, Kanai M, Shibasaki M. Angew. Chem. 2010; 122: 1121 Angew. Chem. Int. Ed. 2010; 49: 1103

• 18 Yang W, Cao J, Zhang M, Lan R, Zhu L, Du G, He S, Lee C.-S. J. Org. Chem. 2015; 80: 836

• 19 Lin X, Weng Z. Org. Biomol. Chem. 2015; 13: 3432

• 20 Xu Z.-F, Cai C.-X, Jiang M, Liu J.-T. Org. Lett. 2014; 16: 3436

• 21 Bellavance G, Barriault L. Angew. Chem. 2014; 126: 6819 Angew. Chem. Int. Ed. 2014; 53: 6701

• 22 Hiraoka Y, Kawasaki-Takasuka T, Morizawa Y, Yamazaki T. J. Fluorine Chem. 2015; 179: 71

• 23 Shade RE, Hyde AM, Olsen J.-C, Merlic CA. J. Am. Chem. Soc. 2010; 132: 1202

• 24 Evano G, Blanchard N, Toumi M. Chem. Rev. 2008; 108: 3054

• 25 Chang M.-Y, Tai H.-Y, Tsai C.-Y, Chuang Y.-J, Lin Y.-T. Tetrahedron Lett. 2014; 55: 6482

• 26 Jouvin K, Bayle A, Legrand F, Evano G. Org. Lett. 2012; 14: 1652

• 27 Ma D, Cai Q, Xie X. Synlett 2005; 1767

• 28 Wan J.-P, Wang C, Liu Y. Appl. Organomet. Chem. 2012; 26: 445

• 29 Fang Y, Li C. J. Am. Chem. Soc. 2007; 129: 8092

• 30 Guo X.-K, Zhang L.-B, Wei D, Niu J.-L. Chem. Sci. 2015; 6: 7059

• 31 Sadykov EKh, Lobanova NA, Stankevich VK. Synthesis 2015; 47: 672

• 32 Chung W, Lindovska P, Camp JE. Tetrahedron Lett. 2011; 52: 6785

• 33 Tellam JP, Carbery DR. Tetrahedron Lett. 2011; 52: 6027

• 34 Sultana S, Indukuri K, Deka MJ, Saikia AK. J. Org. Chem. 2013; 78: 12 182

• 35 Silveira-Dorta G, Sousa IJ, Ríos-Luci C, Martín VS, Fernandes MX, Padrón JM. Bioorg. Med. Chem. Lett. 2013; 23: 5382

• 36 Tejedor D, Méndez-Abt G, García-Tellado F. Chem.–Eur. J. 2010; 16: 428

• 37 Tejedor D, Santos-Expósito A, Méndez-Abt G, Ruiz-Pérez C, García-Tellado F. Synlett 2009; 1223

• 38 Oparina LA, Artem’ev AV, Vysotskaya OV, Sterkhova IV, Khutsishvili SS, Smirnov VI, Trofimov BA. ARKIVOC 2015; 330

• 39 Trofimov BA, Oparina LA, Tarasova OA, Artem’ev AV, Kobychev VB, Gatilov YV, Albanov AI, Gusarova NK. Tetrahedron 2014; 70: 5954

• 40 Li DY, Shi KJ, Mao XF, Zhao ZL, Wu XY, Liu PN. Tetrahedron 2014; 70: 7022

• 41 Matake R, Adachi Y, Matsubara H. Green Chem. 2016; 18: 2614

• 42 Kondo M, Kochi T, Kakiuchi F. J. Am. Chem. Soc. 2011; 133: 32

• 43 Lam RH, Walker DB, Tucker MH, Gatus MRD, Bhadbhade M, Messerle BA. Organometallics 2015; 34: 4312

• 44 Veenboer RMP, Dupuy S, Nolan SP. ACS Catal. 2015; 5: 1330

• 45 Corma A, Ruiz VR, Leyva-Pérez A, Sabater MJ. Adv. Synth. Catal. 2010; 352: 1701

• 46 Gómez-Suárez A, Oonishi Y, Martin AR, Nolan SP. Beilstein J. Org. Chem. 2016; 12: 172

• 47 Diéguez-Vázquez A, Tzschucke CC, Crecente-Campo J, McGrath S, Ley SV. Eur. J. Org. Chem. 2009; 1698

• 48 Brinkmann C, Barrett AGM, Hill MS, Procopiou PA, Reid S. Organometallics 2012; 31: 7287

• 49 Rüttinger R, Leutzow J, Wilsdorf M, Wilckens K, Czekelius C. Org. Lett. 2011; 13: 224

• 50 Liu PN, Su FH, Wen TB, Sung HH.-Y, Williams ID, Jia G. Chem.–Eur. J. 2010; 16: 7889

• 51 Chung JYL, Scott JP, Anderson C, Bishop B, Bremeyer N, Cao Y, Chen Q, Dunn R, Kassim A, Lieberman D, Moment AJ, Sheen F, Zacuto M. Org. Process Res. Dev. 2015; 19: 1760

• 52 Diéguez-Vázquez A, Tzschucke CC, Lam WY, Ley SV. Angew. Chem. 2008; 120: 216 Angew. Chem. Int. Ed. 2008; 47: 209

• 53 Seo S.-Y, Yu X, Marks TJ. J. Am. Chem. Soc. 2009; 131: 263

• 54 Benson S, Collin M.-P, Arlt A, Gabor B, Goddard R, Fürstner A. Angew. Chem. 2011; 123: 8898 Angew. Chem. Int. Ed. 2011; 50: 8739

• 55 Rudolph M, Hashmi ASK. Chem. Soc. Rev. 2012; 41: 2448

• 56 Matsuda Y, Koyama T, Kato M, Kawaguchi T, Saikawa Y, Nakata M. Tetrahedron 2015; 71: 2134

• 57 Quadrelli P, Lunghi F, Bovio B, Gautschi W, Caramella P. Eur. J. Org. Chem. 2012; 1418

• 58 Rehbein J, Hiersemann M. Synthesis 2013; 45: 1121

• 59 Davies HML, Kong N, Churchill MR. J. Org. Chem. 1998; 63: 6586

• 60 Franke R, Selent D, Börner A. Chem. Rev. 2012; 112: 5675

• 61 Larrosa I, Romea P, Urpí F. Tetrahedron 2008; 64: 2683

• 62 Hartman RL, Naber JR, Buchwald SL, Jensen KF. Angew. Chem. 2010; 122: 911 Angew. Chem. Int. Ed. 2010; 49: 899

• 63 Webb D, Jamison TF. Chem. Sci. 2010; 1: 675

• 64 Li L, Chu Y, Gao L, Song Z. Chem. Commun. (Cambridge) 2015; 51: 15 546

• 65 Xiong D.-C, Zhang L.-H, Ye X.-S. Org. Lett. 2009; 11: 1709

• 66 Pedzisa L, Vaughn IW, Pongdee R. Tetrahedron Lett. 2008; 49: 4142

• 67 Fuwa H, Sasaki M. Org. Lett. 2008; 10: 2549

• 68 Ebine M, Fuwa H, Sasaki M. Org. Lett. 2008; 10: 2275

• 69 Ishigai K, Fuwa H, Hashizume K, Fukazawa R, Cho Y, Yotsu-Yamashita M, Sasaki M. Chem.–Eur. J. 2013; 19: 5276

• 70 Khatri HR, Nguyen H, Dunaway JK, Zhu J. Chem.–Eur. J. 2015; 21: 13 553

• 71 Yin J, Bai Y, Mao M, Zhu G. J. Org. Chem. 2014; 79: 9179

• 72 Kumar S, Thornton PD, Painter TO, Jain P, Downard J, Douglas JT, Santini C. J. Org. Chem. 2013; 78: 6529

• 73 Pfrengle F, Lentz D, Reissig H.-U. Org. Lett. 2009; 11: 5534

• 74 Pfrengle F, Reissig H.-U. Beilstein J. Org. Chem. 2010; 6: 75

• 75 Ducray R, Boutron P, Didelot M, Germain H, Lach F, Lamorlette M, Legriffon A, Maudet M, Ménard M, Pasquet G, Renaud F, Simpson I, Young GL. Tetrahedron Lett. 2010; 51: 4755

• 76 Guarda EA, Marzari MRB, Frizzo CP, Guarda PM, Zanatta N, Bonacorso HG, Martins MAP. Tetrahedron Lett. 2012; 53: 170

• 77 Bourdon B, Corbet M, Fontaine P, Goekjian PG, Gueyrard D. Tetrahedron Lett. 2008; 49: 747

• 78 Tomas L, Bourdon B, Caille JC, Gueyrard D, Goekjian PG. Eur. J. Org. Chem. 2013; 915

• 79 Corbet M, Bourdon B, Gueyrard D, Goekjian PG. Tetrahedron Lett. 2008; 49: 750

• 80 Tomas L, Boije af Gennäs G, Hiebel MA, Hampson P, Gueyrard D, Pelotier B, Yli-Kauhaluoma J, Piva O, Lord JM, Goekjian PG. Chem.–Eur. J. 2012; 18: 7452

• 81 Habib S, Larnaud F, Pfund E, Lequeux T, Fenet B, Goekjian PG, Gueyrard D. Eur. J. Org. Chem. 2013; 1872

• 82 Pérez Sánchez I, Turos E. Tetrahedron: Asymmetry 2009; 20: 1646

• 83 Lopes NS, Yoshitake AM, Silva AF, Oliveira Jr VX, Silva LS, Pinheiro AAS, Ciscato LFML. Chem. Biol. Drug Des. 2015; 86: 1373

• 84 Wang C, Zong L, Tan C.-H. J. Am. Chem. Soc. 2015; 137: 10 677

• 85 Wang J, Huang K, Liu L, Chang W, Li J. Tetrahedron Lett. 2015; 56: 2659

• 86 Bernat V, Brox R, Heinrich MR, Auberson YP, Tschammer N. ChemMedChem 2015; 10: 566

• 87 Witten MR, Jacobsen EN. Org. Lett. 2015; 17: 2772

• 88 DeBerardinis AM, Raccuia DS, Thompson EN, Maschinot CA, Hadden MK. Eur. J. Med. Chem. 2015; 93: 156

• 89 Rong Z.-Q, Zhang Y, Chua RHB, Pan H.-J, Zhao Y. J. Am. Chem. Soc. 2015; 137: 4944

• 90 Wang P.-S, Lin H.-C, Zhai Y.-J, Han Z.-Y, Gong L.-Z. Angew. Chem. 2014; 126: 12 414 Angew. Chem. Int. Ed. 2014; 53: 12 218

• 91 Murai M, Hosokawa N, Roy D, Takai K. Org. Lett. 2014; 16: 4134

• 92 Fox BM, Sugimoto K, Iio K, Yoshida A, Zhang JK, Li K, Hao X, Labelle M, Smith M.-L, Rubenstein SM, Ye G, McMinn D, Jackson S, Choi R, Shan B, Ma J, Miao S, Matsui T, Ogawa N, Suzuki M, Kobayashi A, Ozeki H, Okuma C, Ishii Y, Tomimoto D, Furakawa N, Tanaka M, Matsushita M, Takahashi M, Inaba T, Sagawa S, Kayser F. J. Med. Chem. 2014; 57: 3464

• 93 Chelliah MV, Eagen K, Guo Z, Chackalamannil S, Xia Y, Tsai H, Greenlee WJ, Ahn H.-S, Kurowski S, Boykow G, Hsieh Y, Chintala M. ACS Med. Chem. Lett. 2014; 5: 561

• 94 G-Dayanandan N, Paulsen JL, Viswanathan K, Keshipeddy S, Lombardo MN, Zhou W, Lamb KM, Sochia AE, Alverson JB, Priestley ND, Wright DL, Anderson AC. J. Med. Chem. 2014; 57: 2643

• 95 Maier L, Hylse O, Nečas M, Trbušek M, Ytre-Arne M, Dalhus B, Bjorås M, Paruch K. Tetrahedron Lett. 2014; 55: 3713

• 96 Thomas AA, Hunt KW, Volgraf M, Watts RJ, Liu X, Vigers G, Smith D, Sammond D, Tang TP, Rhodes SP, Metcalf AT, Brown KD, Otten JN, Burkard M, Cox AA, Geck Do MK, Dutcher D, Rana S, DeLisle RK, Regal K, Wright AD, Groneberg R, Scearce-Levie K, Siu M, Purkey HE, Lyssikatos JP, Gunawardana IW. J. Med. Chem. 2014; 57: 878

• 97 List B, Čorić I, Grygorenko OO, Kaib PSJ, Komarov I, Lee A, Leutzsch M, Pan SC, Tymtsunik AV, van Gemmeren M. Angew. Chem. 2014; 126: 286 Angew. Chem. Int. Ed. 2014; 53: 282

• 98 Lachia M, Wolf HC, De Mesmaeker A. Bioorg. Med. Chem. Lett. 2014; 24: 2123

• 99 Chelliah MV, Chackalamannil S, Xia Y, Greenlee WJ, Ahn H.-S, Kurowski S, Boykow G, Hsieh Y, Chintala M. ACS Med. Chem. Lett. 2014; 5: 183

• 100 Xu H.-C, Campbell JM, Moeller KD. J. Org. Chem. 2014; 79: 379

• 101 Chepiga KM, Feng Y, Brunelli NA, Jones CW, Davies HML. Org. Lett. 2013; 15: 6136

• 102 Filosa R, Peduto A, Aparoy P, Schaible AM, Luderer S, Krauth V, Petronzi C, Massa A, de Rosa M, Reddanna P, Werz O. Eur. J. Med. Chem. 2013; 67: 269

• 103 Krueger AC, Randolph JT, DeGoey DA, Donner PL, Flentge CA, Hutchinson DK, Liu D, Motter CE, Rockway TW, Wagner R, Beno DWA, Koev G, Lim HB, Beyer JM, Mondal R, Liu Y, Kati WM, Longenecker KL, Molla A, Stewart KD, Maring CJ. Bioorg. Med. Chem. Lett. 2013; 23: 3487

• 104 Thakur GA, Bajaj S, Paronis C, Peng Y, Bowman AL, Barak LS, Caron MG, Parrish D, Deschamps JR, Makriyannis A. J. Med. Chem. 2013; 56: 3904

• 105 Gentry PR, Bridges TM, Lamsal A, Vinson PN, Smith E, Chase P, Hodder PS, Engers JL, Niswender CM, Daniels JS, Conn PJ, Wood MR, Lindsley CW. Bioorg. Med. Chem. Lett. 2013; 23: 2996

• 106 Reddy RS, Prasad PK, Ahuja BB, Sudalai A. J. Org. Chem. 2013; 78: 5045

• 107 Devalankar DA, Karabal PU, Sudalai A. Org. Biomol. Chem. 2013; 11: 1280

• 108 Barlind JG, Bauer UA, Birch AM, Birtles S, Buckett LK, Butlin RJ, Davies RDM, Eriksson JW, Hammond CD, Hovland R, Johannesson P, Johansson MJ, Kemmitt PD, Lindmark BT, Morentin Gutierrez P, Noeske TA, Nordin A, O’Donnell CJ, Petersson AU, Redzic A, Turnbull AV, Vinblad J. J. Med. Chem. 2012; 55: 10 610

• 109 Lauer MG, Henderson WH, Awad A, Stambuli JP. Org. Lett. 2012; 14: 6000

• 110 Havare N, Plattner DA. Org. Lett. 2012; 14: 5078

• 111 Wiebe DA, Burton DJ. J. Fluorine Chem. 2012; 139: 4

• 112 Parra J, Mercader JV, Agulló C, Abad-Somovilla A, Abad-Fuentes A. Toxicol. Lett. 2012; 210: 240

• 113 Ciscato LFML, Weiss D, Beckert R, Baader WJ. J. Photochem. Photobiol., A 2011; 218: 41

• 114 Ruchelman AL, Man H.-W, Chen R, Liu W, Lu L, Cedzik D, Zhang L, Leisten J, Collette A, Narla RK, Raymon HK, Muller GW. Bioorg. Med. Chem. 2011; 19: 6356

• 115 Lian Y, Davies HML. J. Am. Chem. Soc. 2011; 133: 11 940

• 116 Kobayashi K, Kozuki T, Fukamachi S, Konishi H. Helv. Chim. Acta 2010; 93: 2086

• 117 Fu J.-Y, Xu X.-Y, Li Y.-C, Huang Q.-C, Wang L.-X. Org. Biomol. Chem. 2010; 8: 4524

• 118 Fackler P, Berthold C, Voss F, Bach T. J. Am. Chem. Soc. 2010; 132: 15 911

• 119 Fonseca GO, Wang Z.-J, Namjoshi OA, Deschamps JR, Cook JM. Tetrahedron Lett. 2015; 56: 3052

• 120 Krüger S, Gaich T. Angew. Chem. 2015; 127: 320 Angew. Chem. Int. Ed. 2015; 54: 315

• 121 Edwankar RV, Edwankar CR, Deschamps JR, Cook JM. J. Org. Chem. 2014; 79: 10 030

• 122 Edwankar RV, Edwankar CR, Deschamps J, Cook JM. Org. Lett. 2011; 13: 5216

• 123 Kerschgens IP, Claveau E, Wanner MJ, Ingemann S, van Maarseveen JH, Hiemstra H. Chem. Commun. (Cambridge) 2012; 48: 12 243

• 124 Wanner MJ, Ingemann S, van Maarseveen JH, Hiemstra H. Eur. J. Org. Chem. 2013; 1100

• 125 Cheng L.-J, Xie J.-H, Chen Y, Wang L.-X, Zhou Q.-L. Org. Lett. 2013; 15: 764

• 126 Yang Z.-Y, Liao H.-Z, Sheng K, Chen Y.-F, Yao Z.-J. Angew. Chem. 2012; 124: 6590 Angew. Chem. Int. Ed. 2012; 51: 6484

• 127 Darses B, Greene AE, Poisson J.-F. J. Org. Chem. 2012; 77: 1710

• 128 Ueno A, Kitawaki T, Chida N. Org. Lett. 2008; 10: 1999

• 129 Hagiwara H, Fukushima M, Kinugawa K, Matsui T, Hoshi T, Suzuki T. Tetrahedron 2011; 67: 4061

• 130 Mondal S, Prathap A, Sureshan KM. J. Org. Chem. 2013; 78: 7690

• 131 Kulkarni MG, Dhondge AP, Borhade AS, Gaikwad DD, Chavhan SW, Shaikh YB, Nigdale VB, Desai MP, Birhade DR, Shinde MP. Eur. J. Org. Chem. 2009; 3875

• 132 Kato D, Sasaki Y, Boger DL. J. Am. Chem. Soc. 2010; 132: 3685

• 133 Sasaki Y, Kato D, Boger DL. J. Am. Chem. Soc. 2010; 132: 13 533

• 134 Brioche JCR, Barker TA, Whatrup DJ, Barker MD, Harrity JPA. Org. Lett. 2010; 12: 4832

• 135 Wilsdorf M, Reissig H.-U. Angew. Chem. 2014; 126: 4420 Angew. Chem. Int. Ed. 2014; 53: 4332

• 136 Hartley RC, Li J, Main CA, McKiernan GJ. Tetrahedron 2007; 63: 4825

• 137 Beadham I, Micklefield J. Curr. Org. Synth. 2005; 2: 231

• 138 Marsini MA, Huang Y, Lindsey CC, Wu K.-L, Pettus TRR. Org. Lett. 2008; 10: 1477

• 139 Shang XS, Li DY, Li NT, Liu PN. Dyes Pigm. 2015; 114: 8

• 140 Meek SJ, O’Brien RV, Llaveria J, Schrock RR, Hoveyda AH. Nature (London) 2011; 471: 461

• 141 Yu C, Wang C, Kyle AF, Jakubec P, Dixon DJ, Schrock RR, Hoveyda AH. Nature (London) 2011; 479: 88

• 142 Takahira Y, Morizawa Y. J. Am. Chem. Soc. 2015; 137: 7031

• 143 Yu M, Ibrahem I, Hasegawa M, Schrock RR, Hoveyda AH. J. Am. Chem. Soc. 2012; 134: 2788

• 144 Koh MJ, Khan RKM, Torker S, Hoveyda AH. Angew. Chem. 2014; 126: 1999 Angew. Chem. Int. Ed. 2014; 53: 1968

• 145 Khan RKM, O’Brien RV, Torker S, Li B, Hoveyda AH. J. Am. Chem. Soc. 2012; 134: 12 774

• 146 Machado AHL, de Sousa MA, Patto DCS, Azevedo LFS, Bombonato FI, Correia CRD. Tetrahedron Lett. 2009; 50: 1222

• 147 Ceccon J, Danoun G, Greene AE, Poisson J.-F. Org. Biomol. Chem. 2009; 7: 2029

• 148 Fuwa H, Naito S, Goto T, Sasaki M. Angew. Chem. 2008; 120: 4815 Angew. Chem. Int. Ed. 2008; 47: 4737

• 149 Alcaide B, Almendros P, Aragoncillo C, Fernández I, Gómez-Campillos G. J. Org. Chem. 2014; 79: 7075

• 150 Al-Hamdan NS, Habib OM, Ibrahim YA, Al-Awadi NA, El-Dusouqui OME. RSC Adv. 2014; 4: 21 023

• 151 Verrier C, Carret S, Poisson J.-F. Org. Lett. 2012; 14: 5122

• 152 Minami Y, Kodama T, Hiyama T. Angew. Chem. 2015; 127: 11 979 Angew. Chem. Int. Ed. 2015; 54: 11 813

• 153 Minami Y, Shiraishi Y, Kodama T, Kanda M, Yamada K, Anami T, Hiyama T. Bull. Chem. Soc. Jpn. 2015; 88: 1388

• 154 Babu MH, Dwivedi V, Kant R, Reddy MS. Angew. Chem. 2015; 127: 3854 Angew. Chem. Int. Ed. 2015; 54: 3783

• 155 Foster RW, Benhamou L, Porter MJ, Bučar D.-K, Hailes HC, Tame CJ, Sheppard TD. Chem.–Eur. J. 2015; 21: 6107

• 156 Anderson KR, Atkinson SLG, Fujiwara T, Giles ME, Matsumoto T, Merifield E, Singleton JT, Saito T, Sotoguchi T, Tornos JA, Way EL. Org. Process Res. Dev. 2010; 14: 58

• 157 Rajaram S, Sigman MS. Org. Lett. 2005; 7: 5473

• 158 Watanabe Y, Shimada N, Anada M, Hashimoto S. Tetrahedron: Asymmetry 2014; 25: 63

• 159 Navarro C, Shapiro ND, Bernasconi M, Horibe T, Toste FD. Tetrahedron 2015; 71: 5800

• 160 Iqbal N, Sperger CA, Fiksdahl A. Eur. J. Org. Chem. 2013; 907

• 161 Siah H.-SM, Kaur M, Iqbal N, Fiksdahl A. Eur. J. Org. Chem. 2014; 1727

• 162 Siah H.-SM, Hogsnes MC, Iqbal N, Fiksdahl A. Tetrahedron 2016; 72: 1058

• 163 Huang X, Zhang L. J. Am. Chem. Soc. 2007; 129: 6398

• 164 Spencer III WT, Levin MD, Frontier AJ. Org. Lett. 2011; 13: 414

• 165 Malona JA, Cariou K, Frontier AJ. J. Am. Chem. Soc. 2009; 131: 7560

• 166 Malona JA, Cariou K, Spencer III WT, Frontier AJ. J. Org. Chem. 2012; 77: 1891

• 167 Tius MA. Chem. Soc. Rev. 2014; 43: 2979

• 168 Wang G, Zou Y, Li Z, Wang Q, Goeke A. Adv. Synth. Catal. 2011; 353: 550

• 169 Ocello R, De Nisi A, Jia M, Yang Q.-Q, Monari M, Giacinto P, Bottoni A, Miscione GP, Bandini M. Chem.–Eur. J. 2015; 21: 18 445

• 170 Hölemann A, Reissig H.-U. Org. Lett. 2003; 5: 1463

• 171 Hölemann A, Reissig H.-U. Synthesis 2004; 1963

• 172 Chen L.-J, Liu J.-T. J. Fluorine Chem. 2009; 130: 329

• 173 Zimmer R. Synthesis 1993; 165

• 174 Brasholz M, Reissig H.-U. Angew. Chem. 2007; 119: 1659 Angew. Chem. Int. Ed. 2007; 46: 1634

• 175 Brasholz M, Dugovic B, Reissig H.-U. Synthesis 2010; 3855

• 176 Schmiedel VM, Stefani S, Reissig H.-U. Beilstein J. Org. Chem. 2013; 9: 2564

• 177 Helms M, Schade W, Pulz R, Watanabe T, Al-Harrasi A, Fišera L, Hlobilová I, Zahn G, Reissig H.-U. Eur. J. Org. Chem. 2005; 1003

• 178 Jasiński M, Lentz D, Moreno-Clavijo E, Reissig H.-U. Eur. J. Org. Chem. 2012; 3304

• 179 Jasiński M, Watanabe T, Reissig H.-U. Eur. J. Org. Chem. 2013; 605

• 180 Parmeggiani C, Cardona F, Giusti L, Reissig H.-U, Goti A. Chem.–Eur. J. 2013; 19: 10 595

• 181 Pulz R, Watanabe T, Schade W, Reissig H.-U. Synlett 2000; 983

• 182 Al-Harrasi A, Bouché L, Zimmer R, Reissig H.-U. Synthesis 2011; 109

• 183 Tap A, Lecourt C, Dhambri S, Arnould M, Galvani G, Nguyen Van Buu O, Jouanneau M, Férézou J.-P, Ardisson J, Lannou M.-I, Sorin G. Chem.–Eur. J. 2016; 22: 4938