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Muñiz, K.: 2018 Science of Synthesis, 2017/4: Catalytic Oxidation in Organic Synthesis DOI: 10.1055/sos-SD-225-00134
Catalytic Oxidation in Organic Synthesis

5.1 Epoxidation of Alkenes

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Editor: Muñiz, K.

Authors: Andries-Ulmer, A.; Bellina, F.; Berkessel, A.; Borrell, M.; Caballero, A.; Calleja, P.; Chemler, S. R.; Chen, P.; Costas, M.; Díaz-Requejo, M. M.; Dorel, R.; Dornan, L. M.; Ebner, D. C.; Echavarren, A. M.; Engler, H.; Esguerra, K. V. N.; Farràs, P.; Funes-Ardoiz, I.; Garrido-Barros, P.; Gimbert-Suriñach, C.; Gómez-Arrayas, R.; Griesbeck, A. G.; Gulder, T.; Hughes, N. L.; Ikariya, T.; Ishihara, K.; Jiao, N.; Kayaki, Y.; Kleczka, M.; Leuther, T. M.; Li, Z.; Liu, G.; Llobet, A.; Lumb, J.-P.; Martínez, C.; Maseras, F.; Muldoon, M. J.; Muñiz, K.; Park, N.; Patel, H. H.; Perego, L. A.; Pérez, P. J.; Race, N. J.; Rodríguez, N.; Sigman, M. S.; Sillner, S.; Singh, F. V.; Stoltz, B. M.; Uyanik, M.; Vicens, L.; Wdowik, T.; Wirth, T.; Wright, A. C.

Title: Catalytic Oxidation in Organic Synthesis

Print ISBN: 9783132012318; Online ISBN: 9783132403710; Book DOI: 10.1055/b-003-129345

1st edition © 2018. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Koch, G.; Molander, G. A.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

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Abstract

The Sharpless, Jacobsen/Katsuki, and Shi epoxidations are frequently applied in the asymmetric epoxidation of relatively electron-rich alkenes. The development and application of these “classics” has been reviewed numerous times. This chapter covers recent advances in the field, e.g. with regard to the extension of asymmetric epoxidation catalysis to hitherto problematic substrate classes, such as non-conjugated terminal alkenes, or homo- and bis-homoallylic alcohols. At the same time, hydrogen peroxide continues to receive increasing attention as an environmentally friendly and economically attractive terminal oxidant. Examples of efficient organocatalytic epoxidation processes are summarized as well. For electron-poor alkenes, e.g. those carrying carbonyl, nitrile, or sulfone acceptor groups, quite remarkable progress has recently been made both in metal and organocatalysis, and the chapter also includes details of methods and protocols in this area.

Key words

alkenes - oxidation - oxiranes - epoxidation - catalysts - enantioselectivity - iron catalysis - manganese catalysis - ruthenium catalysis - titanium catalysis - tungsten catalysis - vanadium catalysis - zirconium catalysis - organocatalysis - enzyme catalysis
 
  • 1 Cangönül A;, Behlendorf M, Gansäuer A, van Gastel M. Inorg. Chem. 2013; 52: 11859
    PubMed
  • 2 Matsumoto K, Katsuki T, Arends IWCE, In: Science of Synthesis: Stereoselective Synthesis de Vries JG. Thieme Stuttgart 2011; 1. 70
  • 3 Matsumoto K, Katsuki T, Arends IWCE, In: Science of Synthesis: Stereoselective Synthesis de Vries JG. Thieme Stuttgart 2011; 1. 82
  • 4 Matsumoto K, Katsuki T, Arends IWCE, In: Science of Synthesis: Stereoselective Synthesis de Vries JG. Thieme Stuttgart 2011; 1. 105
  • 5 Matsumoto K, Katsuki T, Arends IWCE, In: Science of Synthesis: Stereoselective Synthesis de Vries JG. Thieme Stuttgart 2011; 1. 69
  • 6 Xia F, Ye S, In: Science of Synthesis: Metal-Catalyzed Cyclization Reactions Ma S, Gao S. Thieme Stuttgart 2016; 2. 1
  • 7 Adolfsson H, In: Science of Synthesis Forsyth CJ, Jacobsen EN. 2008; 37. 227
  • 8 Goeddel D, Shi Y, In: Science of Synthesis Forsyth CJ, Jacobsen EN. 2008; 37. 277
  • 9 Sawada Y, Matsumoto K, Kondo S, Watanabe H, Ozawa T, Suzuki K, Saito B, Katsuki T. Angew. Chem. Int. Ed. 2006; 45: 3478
    PubMed
  • 10 Talsi EP, Samsonenko DG, Bryliakov KP. Chem.–Eur. J. 2014; 20: 14329
    PubMed
  • 11 Jat JL, De SR, Kumar G, Adebesin AM, Gandham SK, Falck JR. Org. Lett. 2015; 17: 1058
    PubMed
  • 12 Larivee A, Unger JB, Thomas M, Wirtz C, Dubost C, Handa S, Fürstner A. Angew. Chem. Int. Ed. 2011; 50: 304
    PubMed
  • 13 Matsumoto K, Sawada Y, Saito B, Sakai K, Katsuki T. Angew. Chem. Int. Ed. 2005; 44: 4935
    PubMed
  • 14 Xiong D, Hu X, Wang S, Miao C, Xia C, Sun W. Eur. J. Org. Chem. 2011; 4289
  • 15 Matsumoto K, Feng C, Handa S, Oguma T, Katsuki T. Tetrahedron 2011; 67: 6474
  • 16 Eckert PK, Schill V, Strohmann C. Inorg. Chim. Acta 2011; 376: 634
  • 17 Berkessel A, Ong M.-C, Nachi M, Neudörfl J.-M. ChemCatChem 2010; 2: 1215
  • 18 Berkessel A, Günther T, Wang Q, Neudörfl J.-M. Angew. Chem. Int. Ed. 2013; 52: 8467
    PubMed
  • 19 Wang Q, Neudörfl J.-M, Berkessel A. Chem.–Eur. J. 2015; 21: 247
    PubMed
  • 20 Lansing M, Engler H, Leuther TM, Neudörfl J.-M, Berkessel A. ChemCatChem 2016; 8: 3706
  • 21 Talsi EP, Bryliakova AA, Bryliakov KP. Chem. Rec. 2016; 16: 924
    PubMed
  • 22 Amiri N, Le Maux P, Srour H, Nasri H, Simonneaux G. Tetrahedron 2014; 70: 8836
  • 23 Le Maux P, Srour HF, Simonneaux G. Tetrahedron 2012; 68: 5824
  • 24 Francis MB, Jacobsen EN. Angew. Chem. Int. Ed. 1999; 38: 937
    PubMed
  • 25 Gelalcha FG, Gopinatan A, Bitterlich B, Tse MK, Beller M. Angew. Chem. Int. Ed. 2007; 46: 7293
    PubMed
  • 26 Cussó O, Ribas X, Costas M. Chem. Commun. (Cambridge) 2015; 51: 14285
    PubMed
  • 27 De Faveri G, Ilyashenko G, Watkinson M. Chem. Soc. Rev. 2011; 40: 1722
    PubMed
  • 28 Chen Z, Yin G. Chem. Soc. Rev. 2015; 44: 1083
    PubMed
  • 29 Darwish M, Wills M. Catal. Sci. Technol. 2012; 2: 243
  • 30 Fingerhut A, Serdyuk OV, Tsogoeva SB. Green Chem. 2015; 17: 2042
  • 31 Bryliakov KP, Talsi EP. Coord. Chem. Rev. 2014; 276: 73
  • 32 McDonald AR, Que Jr L. Coord. Chem. Rev. 2013; 257: 414
  • 33 Talsi EP, Bryliakov KP. Coord. Chem. Rev. 2012; 256: 1418
  • 34 Yeung H.-L, Sham K.-C, Tsang C.-S, Lau T.-C, Kwong H.-L. Chem. Commun. (Cambridge) 2008; 3801
    PubMed
  • 35 Cussó O, Garcia-Bosch I, Ribas X, Lloret-Fillol J, Costas M. J. Am. Chem. Soc. 2013; 135: 14871
    PubMed
  • 36 Lyakin OY, Ottenbacher RV, Bryliakov KP, Talsi EP. ACS Catal. 2012; 2: 1196
  • 37 Cussó O, Ribas X, Lloret-Fillol J, Costas M. Angew. Chem. Int. Ed. 2015; 54: 2729
    PubMed
  • 38 Lyakin OY, Bryliakov KP, Britovsek GJP, Talsi EP. J. Am. Chem. Soc. 2009; 131: 10798
    PubMed
  • 39 Lyakin OY, Bryliakov KP, Talsi EP. Inorg. Chem. 2011; 50: 5526
    PubMed
  • 40 Wang Y, Janardanan D, Usharani D, Han K, Que Jr L, Shaik S. ACS Catal. 2013; 3: 1334
  • 41 Oloo WN, Meier KK, Wang Y, Shaik S, Münck E, Que Jr L. Nat. Commun. 2014; 5: 3046
    PubMed
  • 42 Oloo WN, Que Jr L. Acc. Chem. Res. 2015; 48: 2612
    PubMed
  • 43 Lyakin OY, Zima AM, Samsonenko DG, Bryliakov KP, Talsi EP. ACS Catal. 2015; 5: 2702
  • 44 Zhang W, Loebach JL, Wilson SR, Jacobsen EN. J. Am. Chem. Soc. 1990; 112: 2801
  • 45 Shi Q.-P, Shi Z.-H, Li N.-G, Tang Y.-P, Li W, Tang H, Zhang W, Shen M.-Z, Duan J.-A. Curr. Org. Chem. 2013; 17: 2936
  • 46 Shi Z.-H, Li N.-G, Shi Q.-P, Tang Y.-P, Tang H, Shen M.-Z, Duan J.-A. Curr. Org. Chem. 2014; 11: 204
  • 47 Cheng T, Zhao Q, Zhang D, Liu G. Green Chem. 2015; 17: 2100
  • 48 Krishnan KK, Thomas AM, Sindhu KS, Anilkumar G. Tetrahedron 2016; 72: 1
  • 49 Saisaha P, de Boer JW, Browne WR. Chem. Soc. Rev. 2013; 42: 2059
    PubMed
  • 50 Teixeira F, Cordeiro MNDS. Catalysts 2017; 7: 2
  • 51 Hughes DL, Smith GB, Liu J, Dezeny GC, Senanayake CH, Larsen RD, Verhoeven TR, Reider PJ. J. Org. Chem. 1997; 62: 2222
    PubMed
  • 52 Chen L, Cheng F, Jia L, Wang L, Wei J, Zhang J, Yao L, Tang N, Wu J. Appl. Catal., A 2012; 415–416: 40
  • 53 Ruffo F, Bismuto A, Carpentieri A, Cucciolito ME, Lega M, Tuzi A. Inorg. Chim. Acta 2013; 405: 288
  • 54 Chen L, Wei J, Tang N, Cheng F. Catal. Lett. 2012; 142: 486
  • 55 Liao S, List B. Angew. Chem. Int. Ed. 2010; 49: 628
    PubMed
  • 56 Jacobsen EN, Zhang W, Muci AR, Ecker JR, Deng L. J. Am. Chem. Soc. 1991; 113: 7063
  • 57 Huang X, Fu X, Jia Z, Miao Q, Wang G. Sci. China: Chem. 2013; 56: 604
  • 58 Kureshy RI, Roy T, Khan N.-uH, Abdi SHR, Sadhukhan A, Bajaj HC. J. Catal. 2012; 286: 41
  • 59 Huang X, Fu X, Wu X, Jia Z. Tetrahedron Lett. 2013; 54: 4041
  • 60 Huang X, Fu X, Jia Z, Miao Q, Wang G. Catal. Sci. Technol. 2013; 3: 415
  • 61 Maity NC, Abdi SHR, Kureshy RI, Khan N.-uH, Suresh E, Dangi GP, Bajaj HC. J. Catal. 2011; 277: 123
  • 62 Konsler RG, Karl J, Jacobsen EN. J. Am. Chem. Soc. 1998; 120: 10780
  • 63 Bogaerts T, Wouters S, Van Der Voort P, Van Speybroeck V. J. Mol. Catal. A: Chem. 2015; 406: 106
  • 64 Kuźniarska-Biernacka I, Silva AR, Carvalho AP, Pires J, Freire C. Catal. Lett. 2009; 134: 63
  • 65 La Paglia Fragola V, Lupo F, Pappalardo A, Trusso Sfrazzetto G, Toscano RM, Ballistreri FP, Tomaselli GA, Gulino A. J. Mater. Chem. 2012; 22: 20561
  • 66 Ji R, Yu K, Lou L.-L, Liu S. J. Mol. Catal. A: Chem. 2013; 378: 7
  • 67 Song F, Wang C, Falkowski JM, Ma L, Lin W. J. Am. Chem. Soc. 2010; 132: 15390
    PubMed
  • 68 Wei S, Tang Y, Xu X, Xu G, Yu Y, Sun Y, Zheng Y. Appl. Organomet. Chem. 2011; 25: 146
  • 69 Huang J, Fu X, Wang G, Ge Y, Miao Q. Catal. Sci. Technol. 2012; 2: 1040
  • 70 Huang J, Yuan L, Cai J, Chen X, Qi D. Inorg. Chem. Commun. 2016; 65: 4
  • 71 Feichtinger D, Plattner DA. Angew. Chem. Int. Ed. Engl. 1997; 36: 1718
  • 72 Lee NH, Jacobsen EN. Tetrahedron Lett. 1991; 32: 6533
  • 73 Linde C, Arnold M, Åkermark B, Norrby P.-O. Angew. Chem. Int. Ed. Engl. 1997; 36: 1723
  • 74 Linker T. Angew. Chem. Int. Ed. Engl. 1997; 36: 2060
  • 75 Fu H, Look GC, Zhang W, Jacobsen EN, Wong CH. J. Org. Chem. 1991; 56: 6497
  • 76 Linde C, Koliaï N, Norrby P.-O, Åkermark B. Chem.–Eur. J. 2002; 8: 2568
    PubMed
  • 77 Dai W, Li J, Li G, Yang H, Wang L, Gao S. Org. Lett. 2013; 15: 4138
    PubMed
  • 78 Dai W, Shang S, Chen B, Li G, Wang L, Ren L, Gao S. J. Org. Chem. 2014; 79: 6688
    PubMed
  • 79 Shen D, Qiu B, Xu D, Miao C, Xia C, Sun W. Org. Lett. 2016; 18: 372
    PubMed
  • 80 Farokhi A, Hosseini-Monfared H. New J. Chem. 2016; 40: 5032
  • 81 Ottenbacher RV, Bryliakov KP, Talsi EP. Inorg. Chem. 2010; 49: 8620
    PubMed
  • 82 Groves JT, Lee JB, Marla SS. J. Am. Chem. Soc. 1997; 119: 6269
  • 83 Ottenbacher RV, Samsonenko DG, Talsi EP, Bryliakov KP. ACS Catal. 2014; 4: 1599
  • 84 Ottenbacher RV, Samsonenko DG, Talsi EP, Bryliakov KP. ACS Catal. 2016; 6: 979
  • 85 Lai T.-S, Zhang R, Cheung K.-K, Kwong H.-L, Che C.-M. Chem. Commun. (Cambridge) 1998; 1583
  • 86 Döbler C, Mehltretter G, Beller M. Angew. Chem. Int. Ed. 1999; 38: 3026
    PubMed
  • 87 Koya S, Nishioka Y, Mizoguchi H, Uchida T, Katsuki T. Angew. Chem. Int. Ed. 2012; 51: 8243
    PubMed
  • 88 Uchida T, Katsuki T. J. Synth. Org. Chem., Jpn. 2013; 71: 1126
  • 89 Fackler P, Berthold C, Voss F, Bach T. J. Am. Chem. Soc. 2010; 132: 15911
    PubMed
  • 90 Fackler P, Huber SM, Bach T. J. Am. Chem. Soc. 2012; 134: 12869
    PubMed
  • 91 Wong OA, Shi Y. Chem. Rev. 2008; 108: 3958
    PubMed
  • 92 Wong OA, Ramirez TA, Shi Y, In: Science of Synthesis: Asymmetric Organocatalysis List B. Thieme Stuttgart 2012; 1. 783
  • 93 Vega-Pérez JM, Vega-Holm M, Periñán I, Palo-Nieto C, Iglesias-Guerra F. Tetrahedron 2011; 67: 364
  • 94 Vega-Pérez JM, Periñán I, Vega-Holm M, Palo-Nieto C, Iglesias-Guerra F. Tetrahedron 2011; 67: 7057
  • 95 Day DP, Sellars PB. Eur. J. Org. Chem. 2017; 1034
  • 96 Bulman Page PC, Bartlett CJ, Chan Y, Allin SM, McKenzie MJ, Lacour J, Jones GA. Org. Biomol. Chem. 2016; 14: 4220
    PubMed
  • 97 Bulman Page PC, Appleby LF, Day D, Chan Y, Buckley BR, Allin SM, McKenzie MJ. Org. Lett. 2009; 11: 1991
    PubMed
  • 98 Bulman Page PC, Buckley BR, Barros D, Blacker AJ, Heaney H, Marples BA. Tetrahedron 2006; 62: 6607
  • 99 Bartlett CJ, Day DP, Chan Y, Allin SM, McKenzie MJ, Slawin AMZ, Bulman Page PC. J. Org. Chem. 2012; 77: 772
    PubMed
  • 100 Bulman Page PC, Buckley BR, Farah MM, Blacker AJ. Eur. J. Org. Chem. 2009; 3413
  • 101 Fasan R. ACS Catal. 2012; 2: 647
  • 102 Hrycay EG, Bandiera SM. Adv. Exp. Med. Biol. 2015; 851: 1
    PubMed
  • 103 Li AT, Li Z, In: Science of Synthesis: Biocatalysis in Organic Synthesis Faber K, Fessner W.-D, Turner NJ. Thieme Stuttgart 2015; 2. 479
  • 104 Bühler B, Bühler K, Hollmann F, In: Enzyme Catalysis in Organic Synthesis Drauz K, Gröger H, May O. Wiley-VCH Weinheim, Germany 2012; 3. 1278
  • 105 Carballeira JD, Quezada MA, Hoyos P, Simeó Y, Hernaiz MJ, Alcantara AR, Sinisterra JV. Biotechnol. Adv. 2009; 27: 686
    PubMed
  • 106 Li A, Liu J, Pham SQ, Li Z. Chem. Commun. (Cambridge) 2013; 49: 11572
    PubMed
  • 107 Wang B, Li C, Dubey KD, Shaik S. J. Am. Chem. Soc. 2015; 137: 7379
    PubMed
  • 108 Lin H, Liu J.-Y, Wang H.-B, Ahmed AAQ, Wu Z.-L. J. Mol. Catal. B: Enzym. 2011; 72: 77
  • 109 Kuhn D, Kholiq MA, Heinzle E, Bühler B, Schmid A. Green Chem. 2010; 12: 815
  • 110 Lin H, Qiao J, Liu Y, Wu Z.-L. J. Mol. Catal. B: Enzym. 2010; 67: 236
  • 111 Minami A, Shimaya M, Suzuki G, Migita A, Shinde SS, Sato K, Watanabe K, Tamura T, Oguri H, Oikawa H. J. Am. Chem. Soc. 2012; 134: 7246
    PubMed
  • 112 Wu J, Liu C, Jiang Y, Hu M, Li S, Zhai Q. Catal. Commun. 2010; 11: 727
  • 113 Ramón DJ, Yus M. Chem. Rev. 2006; 106: 2126
    PubMed
  • 114 Katsuki T, Martin VS. Org. React. (N. Y.) 1995; 48: 1
  • 115 Heravi MM, Lashaki TB, Poorahmad N. Tetrahedron: Asymmetry 2015; 26: 405
  • 116 Ji N, Yuan J, Liu M, Lan T, He W. Chem. Commun. (Cambridge) 2016; 52: 7731
    PubMed
  • 117 Li Z, Yamamoto H. Acc. Chem. Res. 2013; 46: 506
    PubMed
  • 118 Olivares-Romero JL, Li Z, Yamamoto H. J. Am. Chem. Soc. 2013; 135: 3411
    PubMed
  • 119 Li Z, Yamamoto H. J. Am. Chem. Soc. 2010; 132: 7878
    PubMed
  • 120 Olivares-Romero JL, Li Z, Yamamoto H. J. Am. Chem. Soc. 2012; 134: 5440
    PubMed
  • 121 Licini G, Conte V, Coletti A, Mba M, Zonta C. Coord. Chem. Rev. 2011; 255: 2345
  • 122 Noji M, Kobayashi T, Uechi Y, Kikuchi A, Kondo H, Sugiyama S, Ishii K. J. Org. Chem. 2015; 80: 3203
    PubMed
  • 123 Wang C, Yamamoto H. J. Am. Chem. Soc. 2014; 136: 1222
    PubMed
  • 124 Murphy A, Dubois G, Stack TDP. J. Am. Chem. Soc. 2003; 125: 5250
    PubMed
  • 125 Murphy A, Pace A, Stack TDP. Org. Lett. 2004; 6: 3119
    PubMed
  • 126 Murphy A, Stack TDP. J. Mol. Catal. A: Chem. 2006; 251: 78
  • 127 Wang B, Miao C, Wang S, Xia C, Sun W. Chem.–Eur. J. 2012; 18: 6750
    PubMed
  • 128 Wang X, Miao C, Wang S, Xia C, Sun W. ChemCatChem 2013; 5: 2489
  • 129 Shen D, Miao C, Wang S, Xia C, Sun W. Eur. J. Inorg. Chem. 2014; 5777
  • 130 Sin N, Kim KB, Elofsson M, Meng L, Auth H, Kwok BHB, Crews CM. Bioorg. Med. Chem. Lett. 1999; 9: 2283
  • 131 Cussó O, Garcia-Bosch I, Font D, Ribas X, Lloret-Fillol J, Costas M. Org. Lett. 2013; 15: 6158
    PubMed
  • 132 White MC, Doyle AG, Jacobsen EN. J. Am. Chem. Soc. 2001; 123: 7194
    PubMed
  • 133 Gopalaiah K. Chem. Rev. 2013; 113: 3248
    PubMed
  • 134 Gelalcha FG. Adv. Synth. Catal. 2014; 356: 261
  • 135 Wang C, Yamamoto H. Chem.–Asian J. 2015; 10: 2056
    PubMed
  • 136 Dai W, Li G, Chen B, Wang L, Gao S. Org. Lett. 2015; 17: 904
    PubMed
  • 137 Wang B, Wang S, Xia C, Sun W. Chem.–Eur. J. 2012; 18: 7332
    PubMed
  • 138 Nishikawa Y, Yamamoto H. J. Am. Chem. Soc. 2011; 133: 8432
    PubMed
  • 139 Luo L, Yamamoto H. Eur. J. Org. Chem. 2014; 7803
  • 140 Cussó O, Cianfanelli M, Ribas X, Klein Gebbink RJM, Costas M. J. Am. Chem. Soc. 2016; 138: 2732
    PubMed
  • 141 Bougauchi M, Watanabe S, Arai T, Sasai H, Shibasaki M. J. Am. Chem. Soc. 1997; 119: 2329
  • 142 Nemoto T, Ohshima T, Yamaguchi K, Shibasaki M. J. Am. Chem. Soc. 2001; 123: 2725
    PubMed
  • 143 Kakei H, Tsuji R, Ohshima T, Shibasaki M. J. Am. Chem. Soc. 2005; 127: 8962
    PubMed
  • 144 Colonna S, Perdicchia D, In: Science of Synthesis: Stereoselective Synthesis de Vries JG. Thieme Stuttgart 2011; 1. 123
  • 145 Qian Q, Tan Y, Zhao B, Feng T, Shen Q, Yao Y. Org. Lett. 2014; 16: 4516
    PubMed
  • 146 Chu Y, Liu X, Li W, Hu X, Lin L, Feng X. Chem. Sci. 2012; 3: 1996
  • 147 Chu Y, Hao X, Lin L, Chen W, Li W, Tan F, Liu X, Feng X. Adv. Synth. Catal. 2014; 356: 2214
  • 148 Dandia A, Singh R, Saha M, Shivpuri A. Pharmazie 2002; 57: 602
  • 149 Juliá S, Masana J, Vega JC. Angew. Chem. Int. Ed. Engl. 1980; 19: 929
  • 150 Weiss KM, Tsogoeva SB. Chem. Rec. 2011; 11: 18
    PubMed
  • 151 Zhu YG, Wang Q, Cornwall RG, Shi Y. Chem. Rev. 2014; 114: 8199
    PubMed
  • 152 Nagano M, Doi M, Kurihara M, Suemune H, Tanaka M. Org. Lett. 2010; 12: 3564
    PubMed
  • 153 Akagawa K, Kudo K. Adv. Synth. Catal. 2011; 353: 843
  • 154 Demizu Y, Yamagata N, Nagoya S, Sato Y, Doi M, Tanaka M, Nagasawa K, Okuda H, Kurihara M. Tetrahedron 2011; 67: 6155
  • 155 Miranda R.-A, Llorca J, Medina F, Sueiras JE, Segarra AM. J. Catal. 2011; 282: 65
  • 156 Yamagata N, Demizu Y, Sato Y, Doi M, Tanaka M, Nagasawa K, Okuda H, Kurihara M. Tetrahedron Lett. 2011; 52: 798
  • 157 Akagawa K, Hirata T, Kudo K. Synlett 2016; 27: 1217
  • 158 Weyer A, Díaz D, Nierth A, Schlörer NE, Berkessel A. ChemCatChem 2012; 4: 337
  • 159 Berkessel A, Gasch N, Glaubitz K, Koch C. Org. Lett. 2001; 3: 3839
    PubMed
  • 160 Berkessel A, Koch B, Toniolo C, Rainaldi M, Broxterman QB, Kaptein B. Biopolymers 2006; 84: 90
    PubMed
  • 161 Wakeham D, Crivoi DG, Medina F, Segarra AM, Rutland MW. J. Colloid Interface Sci. 2016; 469: 263
    PubMed
  • 162 Davis RL, Stiller J, Naicker T, Jiang H, Jørgensen KA. Angew. Chem. Int. Ed. 2014; 53: 7406
    PubMed
  • 163 Meninno S, Lattanzi A. Catal. Today 2017; 285: 39
  • 164 Hashimoto T, Maruoka K. Chem. Rev. 2007; 107: 5656
    PubMed
  • 165 Ooi T, Maruoka K. Angew. Chem. Int. Ed. 2007; 46: 4222
    PubMed
  • 166 Marigo M, Franzén J, Poulsen TB, Zhuang W, Jørgensen KA. J. Am. Chem. Soc. 2005; 127: 6964
    PubMed
  • 167 Lattanzi A. Chem. Commun. (Cambridge) 2009; 1452
    PubMed
  • 168 Lee S, MacMillan DWC. Tetrahedron 2006; 62: 11413
  • 169 Wang X, List B. Angew. Chem. Int. Ed. 2008; 47: 1119
    PubMed
  • 170 Wang X, Reisinger CM, List B. J. Am. Chem. Soc. 2008; 130: 6070
    PubMed
  • 171 Sparr C, Schweizer WB, Senn HM, Gilmour R. Angew. Chem. Int. Ed. 2009; 48: 3065
    PubMed
  • 172 Russo A, Lattanzi A. Org. Biomol. Chem. 2010; 8: 2633
    PubMed
  • 173 De Fusco C, Tedesco C, Lattanzi A. J. Org. Chem. 2011; 76: 676
    PubMed
  • 174 Russo A, Lattanzi A. Synthesis 2009; 1551
  • 175 Zhao G.-L, Ibrahem I, Sundén H, Córdova A. Adv. Synth. Catal. 2007; 349: 1210
  • 176 Deobald AM, Corrêa AG, Rivera DG, Paixão MW. Org. Biomol. Chem. 2012; 10: 7681
    PubMed
  • 177 Egger J, Bretscher P, Freigang S, Kopf M, Carreira EM. Angew. Chem. Int. Ed. 2013; 52: 5382
    PubMed
  • 178 Lee A, Reisinger CM, List B. Adv. Synth. Catal. 2012; 354: 1701
  • 179 Lifchits O, Mahlau M, Reisinger CM, Lee A, Fares C, Polyak I, Gopakumar G, Thiel W, List B. J. Am. Chem. Soc. 2013; 135: 6677
    PubMed
  • 180 Lifchits O, Reisinger CM, List B. J. Am. Chem. Soc. 2010; 132: 10227
    PubMed
  • 181 Russo A, Galdi G, Croce G, Lattanzi A. Chem.–Eur. J. 2012; 18: 6152
    PubMed
  • 182 Meninno S, Vidal-Albalat A, Lattanzi A. Org. Lett. 2015; 17: 4348
    PubMed
  • 183 Meninno S, Zullo L, Overgaard J, Lattanzi A. Adv. Synth. Catal. 2017; 359: 913
  • 184 Kawai H, Okusu S, Yuan Z, Tokunaga E, Yamano A, Shiro M, Shibata N. Angew. Chem. Int. Ed. 2013; 52: 2221
    PubMed
  • 185 Wu S, Pan D, Cao C, Wang Q, Chen F.-X. Adv. Synth. Catal. 2013; 355: 1917
  • 186 Vidal-Albalat A, Świderek K, Izquierdo J, Rodríguez S, Moliner V, González FV. Chem. Commun. (Cambridge) 2016; 52: 10060
    PubMed
  • 187 Allingham MT, Bennett EL, Davies DH, Harper PM, Howard-Jones A, Mehdar YTH, Murphy PJ, Thomas DA, Caulkett PWR, Potter D, Lam CM, OʼDonoghue AC. Tetrahedron 2016; 72: 496