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Synthesis 2013; 45(16): 2201-2221
DOI: 10.1055/s-0033-1338491
DOI: 10.1055/s-0033-1338491
review
Allylic Oxidations of Olefins to Enones
Further Information
Publication History
Received: 28 February 2013
Accepted after revision: 16 April 2013
Publication Date:
17 July 2013 (online)
Abstract
Allylic oxidations of olefins to enones are C–H functionalizations and are valuable organic transformations that permit the synthesis of value-added products from simple precursors. A variety of stoichiometric and catalytic metal-based methods are available for these conversions. In addition, metal-free and biocatalytic protocols are gaining in importance. This review summarizes the available oxidation methods and compares their regio- and chemoselectivities.
1 Introduction
2 Chromium-Based Oxidation
2.1 Stoichiometric Methods
2.2 Catalytic Methods
2.3 Chromium on Solid Support
3 Regio- and Chemoselectivity of Allylic Oxidations
4 Other Metal-Based Oxidations
4.1 Copper Reagents
4.2 Rhodium Reagents
4.3 Selenium Reagents
4.4 Cobalt Reagents
4.5 Ruthenium Reagents
4.6 Palladium Reagents
4.7 Iron Reagents
4.8 Other Metal Reagents
5 Metal-Free and Biocatalytic Methods
5.1 Metal-Free Methods
5.2 Biocatalytic Methods
6 Conclusion
-
References
- 1 Wilberg KB. Oxidation in Organic Chemistry . Academic Press; New York: 1965
- 2 Cainelli G, Cardille G. Chromium in Oxidation Chemistry . Springer Verlag; Berlin: 1984
- 3 Page PC. B, McCarthy TJ In Comprehensive Organic Synthesis . Trost BM, Fleming I. Pergamon; Oxford: 1991: 83
- 4 Roduner E, Kaim W, Sarkar B, Urlacher VB, Pleiss J, Gläser R, Einicke W.-H, Sprenger GA, Beifuß U, Klemm E, Liebner C, Hieronymus H, Hsu S.-F, Plietker B, Laschat S. ChemCatChem 2013; 5: 82
- 5 Dauben WG, Lorber ME, Fullerton DS. J. Org. Chem. 1969; 34: 3587
- 6 Joseph T, Sawant DP, Gopinath CS, Halligudi SB. J. Mol. Catal. A: Chem. 2002; 184: 289
- 7 Rothenberg G, Yatziv Y, Sasson Y. Tetrahedron 1998; 54: 593
- 8 Smith AB, Konopelski JP. J. Org. Chem. 1984; 49: 4094
- 9 Berger R. Biotechnol. Lett. 2009; 31: 1651
- 10 Hanson JR. Nat. Prod. Rep. 2007; 24: 1342
- 11 Rispens MT, Zondervan C, Feringa BL. Tetrahedron: Asymmetry 1995; 6: 661
- 12 Andrus MB, Lashley JC. Tetrahedron 2002; 58: 845
- 13 Moiseev II, Vargaftik MN. Coord. Chem. Rev. 2004; 248: 2381
- 14 Christie SD. R, Warrington AD. Synthesis 2008; 1325
- 15 Kharasch MS, Sosnovsky G. J. Am. Chem. Soc. 1958; 80: 756
- 17 Salvador JA. R, Silvestre SM, Moreira VM. Curr. Org. Chem. 2006; 10: 2227
- 18 Salvador JA. R, Silvestre SM, Moreira VM. Curr. Org. Chem. 2008; 12: 492
- 19 Salvador JA. R, Silvestre SM, Moreira VM. Curr. Org. Chem. 2012; 16: 1243
- 20 Nakamura A, Nakada M. Synthesis 2013; 45: 1421
- 21 Catino AJ, Forslund RE, Doyle MP. J. Am. Chem. Soc. 2004; 126: 13622
- 22 Muzart J. Bull. Soc. Chim. Fr. 1986; 65
- 23 Butenandt A, Hausmann E, Paland J. Ber. Dtsch. Chem. Ges. 1938; 71: 1316
- 24 Heusler K, Wettstein A. Helv. Chim. Acta 1952; 35: 284
- 25 Marshall CW, Ray RE, Laos I, Riegel B. J. Am. Chem. Soc. 1957; 79: 6308
- 26 Fullerton DS, Chen C.-M. Synth. Commun. 1976; 6: 217
- 27 Parish EJ, Chitrakorn S, Taylor FR, Saucier SE. Chem. Phys. Lipids 1984; 36: 179
- 28 Chorvat RJ, Desai BN. J. Org. Chem. 1979; 44: 3974
- 29 Parish EJ, Chitrakorn S, Todd KL. Org. Prep. Proced. Int. 1985; 17: 192
- 30 Marwah P, Lardy HA. (Humanetics Corporation). US Patent 6384251 B1, 2002
- 31 Parish EJ, Chitrakorn S, Wei T.-Y. Synth. Commun. 1986; 16: 1371
- 32 Parish EJ, Wei T.-Y. Synth. Commun. 1987; 17: 1227
- 33 Chidambaram N, Chandrasekaran S. J. Org. Chem. 1987; 52: 5048
- 34 Bora U, Chaudhuri MK, Dey D, Kalita D, Kharmawphlang W, Mandal GC. Tetrahedron 2001; 57: 2445
- 35 Salvador JA. R, Clark JH. Green Chem. 2002; 4: 352
- 36 Yao Z, Hu X, Mao J, Li H. Green Chem. 2009; 11: 2013
- 37 Zhang P, Wang Y, Yao J, Wang C, Yan C, Antonietti M, Li H. Adv. Synth. Catal. 2011; 353: 1447
- 38 Parish E, Kizito S, Qiu Z. Lipids 2004; 39: 801
- 39 Treibs W, Schmidt H. Ber. Dtsch. Chem. Ges. 1928; 61: 459
- 40 Stavely HE, Bollenback GN. J. Am. Chem. Soc. 1943; 65: 1285
- 41 Heilbron IM, Simpson JC. E, Wilkinson DG. J. Chem. Soc. 1932; 1699
- 42 Reindel F. Liebigs Ann. Chem. 1928; 466: 131
- 43 Whitmore FC, Pedlow GW. J. Am. Chem. Soc. 1941; 63: 758
- 44 Oppenauer RV, Oberrauch H. An. Asoc. Quim. Argent. 1949; 37
- 45 Dauben WG, Ashcraft AC. J. Am. Chem. Soc. 1963; 85: 3673
- 46 Enzell C. Tetrahedron Lett. 1962; 3: 185
- 47 Hunter GL. K, Brogden WB. J. Food Sci. 1965; 30: 876
- 48 Goldblum A, Mechoulam R. J. Chem. Soc., Perkin Trans. 1 1977; 1889
- 49 Mechoulam R, Luchter K, Goldblum A. Synthesis 1974; 363
- 50 Poos GI, Arth GE, Beyler RE, Sarett LH. J. Am. Chem. Soc. 1953; 75: 422
- 51 Holum JR. J. Org. Chem. 1961; 26: 4814
- 52 Marshall JA, Brady SF. J. Org. Chem. 1970; 35: 4068
- 53 Yosioka I, Kimura T. Chem. Pharm. Bull. 1965; 13: 1430
- 54 Collins JC, Hess WW, Frank FJ. Tetrahedron Lett. 1968; 9: 3363
- 55 Salmond WG, Barta MA, Havens JL. J. Org. Chem. 1978; 43: 2057
- 56 Sisler HH, Bush JD, Accountius OE. J. Am. Chem. Soc. 1948; 70: 3827
- 57 Ratcliffe R, Rodehorst R. J. Org. Chem. 1970; 35: 4000
- 58 Corey EJ, Fleet GW. J. Tetrahedron Lett. 1973; 14: 4499
- 59 Schlessinger RH, Wood JL, Poss AJ, Nugent RA, Parsons WH. J. Org. Chem. 1983; 48: 1146
- 60 Liu ZY, Zhou XR, Wu ZM. J. Chem. Soc., Chem. Commun. 1987; 1868
- 61 Yoshida K, Grieco PA. J. Org. Chem. 1984; 49: 5257
- 62 Kok P, Declercq PJ, Vandewalle ME. J. Org. Chem. 1979; 44: 4553
- 63 Magnus P, Leapheart T, Walker C. J. Chem. Soc., Chem. Commun. 1985; 1185
- 64 Harmata M, Bohnert GJ. Org. Lett. 2003; 5: 59
- 65 Humphrey JM, Liao YS, Ali A, Rein T, Wong YL, Chen HJ, Courtney AK, Martin SF. J. Am. Chem. Soc. 2002; 124: 8584
- 66 Parish EJ, Chitrakorn S. Synth. Commun. 1985; 15: 393
- 67 Nagai T, Ogawa K, Morita M, Koyama M, Ando A, Miki T, Kumadaki I. Chem. Pharm. Bull. 1989; 37: 1751
- 68 Corey EJ, Schmidt G. Tetrahedron Lett. 1979; 20: 399
- 69 Corey EJ, Suggs JW. Tetrahedron Lett. 1975; 16: 2647
- 70 Piancatelli G, Scettri A, D’Auria M. Synthesis 1982; 245
- 71 Müller RK, Bernhard K, Kienzle F, Mayer H, Rüttimann A. Food Chem. 1980; 5: 15
- 72 Müller RK, Mayer H, Noack K, Daly JJ, Tauber JD, Liaaen-Jensen S. Helv. Chim. Acta 1978; 61: 2881
- 73 Bonadies F, Di Fabio R, Bonini C. J. Org. Chem. 1984; 49: 1647
- 74 Pearson AJ, Chen Y.-S, Hsu S.-Y, Ray T. Tetrahedron Lett. 1984; 25: 1235
- 75 Pearson AJ, Chen Y.-S, Han GR, Hsu S.-Y, Ray T. J. Chem. Soc., Perkin Trans. 1 1985; 267
- 76 Muzart J. Tetrahedron Lett. 1987; 28: 4665
- 77 Fousteris MA, Koutsourea AI, Nikolaropoulos SS, Riahi A, Muzart J. J. Mol. Catal. A: Chem. 2006; 250: 70
- 78 Muzart J. Synth. Commun. 1989; 19: 2061
- 79 Amann A, Ourisson G, Luu B. Synthesis 1987; 1002
- 80 Majetich G, Jee SS, Ringold C, Nemeth GA. Tetrahedron Lett. 1990; 31: 2239
- 81 Majetich G, Song JS, Ringold C, Nemeth GA, Newton MG. J. Org. Chem. 1991; 56: 3973
- 82 Sheldon RA, Van Doorn JA. J. Catal. 1973; 31: 427
- 83 Indictor N, Jochsberger T. J. Org. Chem. 1966; 31: 4271
- 84 Indictor N, Jochsberger T, Kurnit D. J. Org. Chem. 1969; 34: 2861
- 85 Indictor N, Jochsberger T, Kurnit D. J. Org. Chem. 1969; 34: 2855
- 86 Groves JT, Kruper WJ. J. Am. Chem. Soc. 1979; 101: 7613
- 87 Mansuy D, Leclaire J, Fontecave M, Dansette P. Tetrahedron 1984; 40: 2847
- 88 Traylor TG, Miksztal AR. J. Am. Chem. Soc. 1989; 111: 7443
- 89 Young J.-j, Jung L.-j, Cheng K.-m. Tetrahedron Lett. 2000; 41: 3415
- 90 Dumas F, Thominiaux C, Miet C, d’Angelo J, Desmaële D, Nour M, Cavé C, Morgant G, Tran Huu-Dau M.-E. Tetrahedron Lett. 2002; 43: 9649
- 91 Muzart J. Tetrahedron Lett. 1987; 28: 2131
- 92 Rothenberg G, Wiener H, Sasson Y. J. Mol. Catal. A: Chem. 1998; 136: 253
- 93 Braunstein P, Devenish R, Gallezot P, Heaton BT, Humphreys CJ, Kervennal J, Mulley S, Ries M. Angew. Chem., Int. Ed. Engl. 1988; 27: 927
- 94 Inoue M, Uragaki T, Enomoto S. Chem. Lett. 1986; 15: 2075
- 95 Zhang N, Mann CM, Shapley PA. J. Am. Chem. Soc. 1988; 110: 6591
- 96 Freer VJ, Yates P. Chem. Lett. 1984; 13: 2031
- 97 Baptistella LH. B, Sousa IM. O, Gushikem Y, Aleixo AM. Tetrahedron Lett. 1999; 40: 2695
- 98 Liu J, Zhu H.-Y, Cheng X.-H. Synth. Commun. 2009; 39: 1076
- 99 Lempers HE. B, Sheldon RA. Appl. Catal. A: Gen. 1996; 143: 137
- 100 Dapurkar SE, Sakthivel A, Selvam P. New J. Chem. 2003; 27: 1184
- 101 Sakthivel A, Dapurkar SE, Selvam P. Appl. Catal. A: Gen. 2003; 246: 283
- 102 Murphy EF, Mallat T, Baiker A. Catal. Today 2000; 57: 115
- 103 Gomes Md. F. T, Antunes OA. C. J. Mol. Catal. A: Chem. 1997; 121: 145
- 104 Wiberg KB, Nielsen SD. J. Org. Chem. 1964; 29: 3353
- 105 Arsenou ES, Koutsourea AI, Fousteris MA, Nikolaropoulos SS. Steroids 2003; 68: 407
- 106 Bridger RF, Russell GA. J. Am. Chem. Soc. 1963; 85: 3754
- 107 Howard JA, Ingold KU. Can. J. Chem. 1967; 45: 793
- 108 Russell GA, DeBoer C. J. Am. Chem. Soc. 1963; 85: 3136
- 109 Walling C, Rieger AL, Tanner DD. J. Am. Chem. Soc. 1963; 85: 3129
- 110 Walling C, Thaler W. J. Am. Chem. Soc. 1961; 83: 3877
- 111 Rothenberg G, Sasson Y. Tetrahedron 1998; 54: 5417
- 112 Bernardi R, Caronna T, Coggiola D, Ganazzoli F, Morrocchi S. J. Org. Chem. 1986; 51: 1045
- 113 Bolland JL. Trans. Faraday Soc. 1950; 46: 358
- 114 Beckwith A, Phillipou G. Aust. J. Chem. 1976; 29: 1277
- 115 Salvador JA. R, Sáe Melo ML, Campos Neves AS. Tetrahedron Lett. 1997; 38: 119
- 116 Kimura M, Muto T. Chem. Pharm. Bull. 1979; 27: 109
- 117 Kimura M, Muto T. Chem. Pharm. Bull. 1980; 28: 1836
- 118 Rothenberg G, Feldberg L, Wiener H, Sasson Y. J. Chem. Soc., Perkin Trans. 2 1998; 2429
- 119 Li Y, Wu X, Lee TB, Isbell EK, Parish EJ, Gorden AE. V. J. Org. Chem. 2010; 75: 1807
- 120 Collman JP, Kubota M, Hosking JW. J. Am. Chem. Soc. 1967; 89: 4809
- 121 Dudley C, Read G. Tetrahedron Lett. 1972; 13: 5273
- 122 Kurkov VP, Pasky JZ, Lavigne JB. J. Am. Chem. Soc. 1968; 90: 4743
- 123 Fusi A, Ugo R, Fox F, Pasini A, Cenini S. J. Organomet. Chem. 1971; 26: 417
- 124 Uemura S, Patil SR. Tetrahedron Lett. 1982; 23: 4353
- 125 Reuter JM, Sinha A, Salomon RG. J. Org. Chem. 1978; 43: 2438
- 126 Baldwin JE, Swallow JC. Angew. Chem., Int. Ed. Engl. 1969; 8: 601
- 127 Kraft P, Popaj K. Eur. J. Org. Chem. 2008; 4806
- 128 McLaughlin EC, Choi H, Wang K, Chiou G, Doyle MP. J. Org. Chem. 2008; 74: 730
- 129 Choi H, Doyle MP. Org. Lett. 2007; 9: 5349
- 130 Auterhoff H. Arch. Pharm. 1969; 302: 119
- 131 Schaefer JP, Horvath B, Klein HP. J. Org. Chem. 1968; 33: 2647
- 132 Umbreit MA, Sharpless KB. J. Am. Chem. Soc. 1977; 99: 5526
- 133 Waitkins GR, Clark CW. Chem. Rev. 1945; 36: 235
- 134 Zeecheng KY, Cheng CC. J. Heterocycl. Chem. 1967; 4: 163
- 135 Meinwald J, Opheim K, Eisner T. Tetrahedron Lett. 1973; 281
- 136 Gramatica P, Manitto P, Monti D, Speranza G. Tetrahedron 1987; 43: 4481
- 137 Sakai K, Ohtsuka T, Misumi S, Shirahama H, Matsumoto T. Chem. Lett. 1981; 355
- 138 Bestmann HJ, Ermann P. Liebigs Ann. Chem. 1984; 1740
- 139 Suzuki E, Hamajima R, Inoue S. Synthesis 1975; 192
- 140 Coleman RS, Walczak MC. J. Org. Chem. 2006; 71: 9841
- 141 Barton DH. R, Crich D. Tetrahedron 1985; 41: 4359
- 142 Barton DH. R, Wang T.-L. Tetrahedron Lett. 1994; 35: 5149
- 143 Crich D, Zou Y. Org. Lett. 2004; 6: 775
- 144 Guillemonat A. Ann. Chim. (Rome) 1939; 11: 143
- 145 Tonigold M, Lu Y, Mavrandonakis A, Puls A, Staudt R, Mollmer J, Sauer J, Volkmer D. Chem. Eur. J. 2011; 17: 8671
- 146 Yin C, Yang Z, Li B, Zhang F, Wang J, Ou E. Catal. Lett. 2009; 131: 440
- 147 Hirano M, Nakamura K, Morimoto T. J. Chem. Soc., Perkin Trans. 2 1981; 817
- 148 Morimoto T, Machida T, Hirano M, Zhung X. J. Chem. Soc., Perkin Trans. 2 1988; 909
- 149 Punniyamurthy T, Bhatia B, Iqbal J. Tetrahedron Lett. 1993; 34: 4657
- 150 Punniyamurthy T, Iqbal J. Tetrahedron Lett. 1994; 35: 4003
- 151 Madhava ReddyM, Punniyamurthy T, Iqbal J. Tetrahedron Lett. 1995; 36: 159
- 152 Hay AS. US Patent 2992272, 1961
- 153 Lohri B. US Patent 4393243, 1983
- 154 da Silva MJ, Robles-Dutenhefner P, Menini L, Gusevskaya EV. J. Mol. Catal. A: Chem. 2003; 201: 71
- 155 Robles-Dutenhefner PA, da Silva MJ, Sales LS, Sousa EM. B, Gusevskaya EV. J. Mol. Catal. A: Chem. 2004; 217: 139
- 156 Maksimchuk NV, Melgunov MS, Chesalov YA, Mrowiec-Białoń J, Jarzębski AB, Kholdeeva OA. J. Catal. 2007; 246: 241
- 157 Menini L, Pereira MC, Parreira LA, Fabris JD, Gusevskaya EV. J. Catal. 2008; 254: 355
- 158 Lajunen M, Koskinen AM. P. Tetrahedron Lett. 1994; 35: 4461
- 159 Lajunen MK, Maunula T, Koskinen AM. P. Tetrahedron 2000; 56: 8167
- 160 Jurado-Gonzalez M, Sullivan AC, Wilson JR. H. Tetrahedron Lett. 2003; 44: 4283
- 161 Salvador JA. R, Clark JH. Chem. Commun. 2001; 33
- 162 Silvestre SM, Salvador JA. R, Clark JH. J. Mol. Catal. A: Chem. 2004; 219: 143
- 163 Fang Z, Tang R.-r, Zhang R.-r, Huang K.-l. Bull. Korean Chem. Soc. 2009; 30: 2208
- 164 Silva F, Jacinto M, Landers R, Rossi L. Catal. Lett. 2011; 141: 432
- 165 Groves JT, Quinn R. J. Am. Chem. Soc. 1985; 107: 5790
- 166 Thompson MS, Meyer TJ. J. Am. Chem. Soc. 1982; 104: 4106
- 167 Thompson MS, Meyer TJ. J. Am. Chem. Soc. 1982; 104: 5070
- 168 Seok WK, Dobson JC, Meyer TJ. Inorg. Chem. 1988; 27: 3
- 169 Neumann R, Abu-Gnim C. J. Am. Chem. Soc. 1990; 112: 6025
- 170 Murahashi S.-I, Oda Y, Naota T. Chem. Lett. 1992; 21: 2237
- 171 Murahashi S.-I, Oda Y, Naota T, Kuwabara T. Tetrahedron Lett. 1993; 34: 1299
- 172 Tanaka M, Kobayashi T.-a, Sakakura T. Angew. Chem., Int. Ed. Engl. 1984; 23: 518
- 173 Yu J.-Q, Corey EJ. Org. Lett. 2002; 4: 2727
- 174 Miller RA, Li W, Humphrey GR. Tetrahedron Lett. 1996; 37: 3429
- 175 Harre M, Haufe R, Nickisch K, Weinig P, Weinmann H, Kinney WA, Zhang X. Org. Process Res. Dev. 1998; 2: 100
- 176 Jung ME, Johnson TW. Org. Lett. 1999; 1: 1671
- 177 Kim H.-S, Choi B.-S, Kwon K.-C, Lee S.-O, Kwak HJ, Lee CH. Bioorg. Med. Chem. 2000; 8: 2059
- 178 Shingate BB, Hazra BG, Salunke DB, Pore VS. Tetrahedron Lett. 2011; 52: 6007
- 179 Ito Y, Hirao T, Saegusa T. J. Org. Chem. 1978; 43: 1011
- 180 Theissen RJ. J. Org. Chem. 1971; 36: 752
- 181 Muzart J, Pale P, Pete J.-P. J. Chem. Soc., Chem. Commun. 1981; 668
- 182 Trost BM, Strege PE, Weber L, Fullerton TJ, Dietsche TJ. J. Am. Chem. Soc. 1978; 100: 3407
- 183 Muzart J, Pete JP, Riahi A. J. Organomet. Chem. 1987; 331: 113
- 184 Muzart J, Pale P, Pete J.-P. Tetrahedron Lett. 1982; 23: 3577
- 185 Hosokawa T, Inui S, Murahashi S.-I. Chem. Lett. 1983; 12: 1081
- 186 Yu J.-Q, Corey EJ. J. Am. Chem. Soc. 2003; 125: 3232
- 187 Yu J.-Q, Wu H.-C, Corey EJ. Org. Lett. 2005; 7: 1415
- 188 Islam M, Mondal P, Roy AS, Tuhina K. J. Appl. Polym. Sci. 2010; 118: 52
- 189 Rabe V, Frey W, Baro A, Laschat S. Helv. Chim. Acta 2012; 95: 197
- 190 Barry SM, Mueller-Bunz H, Rutledge PJ. Org. Biomol. Chem. 2012; 10: 7372
- 191 Barton DH. R, Doller D. Acc. Chem. Res. 1992; 25: 504
- 192 O’Reilly E, Köhler V, Flitsch SL, Turner NJ. Chem. Commun. 2011; 47: 2490
- 193 MacFaul PA, Wayner DD. M, Ingold KU. Acc. Chem. Res. 1998; 31: 159
- 194 Birnbaum ER, Grinstaff MW, Labinger JA, Bercaw JE, Gray HB. J. Mol. Catal. A: Chem. 1995; 104: L119
- 195 Tabushi I, Koga N. J. Am. Chem. Soc. 1979; 101: 6456
- 196 Appleton AJ, Evans S, Smith JR. L. J. Chem. Soc., Perkin Trans. 2 1996; 281
- 197 De Poorter B, Meunier B. J. Chem. Soc., Perkin Trans. 2 1985; 1735
- 198 Kalilur Rahiman A, Sreedaran S, Shanmuga Bharathi K, Narayanan V. J. Porous Mater. 2010; 17: 711
- 199 González LM, Villa de P AL, Montes de C C, Sorokin A. Tetrahedron Lett. 2006; 47: 6465
- 200 Połtowicz J, Serwicka EM, Bastardo-Gonzalez E, Jones W, Mokaya R. Appl. Catal., A: Gen. 2001; 218: 211
- 201 Smeureanu G, Aggarwal A, Soll CE, Arijeloye J, Malave E, Drain CM. Chem. Eur. J. 2009; 15: 12133
- 202 Gannon SM, Krause JG. Synthesis 1987; 915
- 203 Noureldin NA, Lee DG. Tetrahedron Lett. 1981; 22: 4889
- 204 Prousa R, Schönecker B. J. Prakt. Chem. 1991; 333: 775
- 205 Pan J.-F, Chen K. J. Mol. Catal. A: Chem. 2001; 176: 19
- 206 Shing TK. M, Ying-Yeung, Su PL. Org. Lett. 2006; 8: 3149
- 207 Salvador JA. R, Silvestre SM, Pinto RM. A. Molecules 2011; 16: 2884
- 208 Salvador JA. R, Silvestre SM. Tetrahedron Lett. 2005; 46: 2581
- 209 Mihelich ED, Eickhoff DJ. J. Org. Chem. 1983; 48: 4135
- 210 Schenck GO, Neumüller OA, Eisfeld W. Liebigs Ann. Chem. 1958; 618: 202
- 211 Ishii Y, Nakayama K, Takeno M, Sakaguchi S, Iwahama T, Nishiyama Y. J. Org. Chem. 1995; 60: 3934
- 212 Marwah P, Marwah A, Lardy HA. Green Chem. 2004; 6: 570
- 213 Marwah P, Lardy HA, Marwah A. US Patent 6274746 B1, 2001
- 214 Silvestre SM, Salvador JA. R. Tetrahedron 2007; 63: 2439
- 215 Marwah P, Lardy HA. (Humanetics Corporation). US Patent 6111118A, 2000
- 216 Zhao Y, Yeung Y.-Y. Org. Lett. 2010; 12: 2128
- 217 Ansari MB, Min B.-H, Mo Y.-H, Park S.-E. Green Chem. 2011; 13: 1416
- 218 Yang G, Zhang Q, Miao H, Tong X, Xu J. Org. Lett. 2004; 7: 263
- 219 Tong X, Xu J, Miao H, Yang G, Ma H, Zhang Q. Tetrahedron 2007; 63: 7634
- 220 Sharma A, Sharma N, Shard A, Kumar R, Mohanakrishnan D, Sinha SA. K, Sahal D. Org. Biomol. Chem. 2011; 9: 5211
- 221 Faber K. Biotransformations in organic chemistry . 3rd ed. Springer; Berlin: 1997
- 222 Kolek T. J. Steroid Biochem. Mol. Biol. 1999; 71: 83
- 223 Fritz-Langhals E, Kunath B. Tetrahedron Lett. 1998; 39: 5955
- 224 Niku-Paavola ML, Viikari L. J. Mol. Catal. B: Enzym. 2000; 10: 435
- 225 Fraatz M, Berger R, Zorn H. Appl. Microbiol. Biotechnol. 2009; 83: 35
- 226 Onken J, Berger RG. J. Biotechnol. 1999; 69: 163
- 227 Rickert A, Krombach V, Hamers O, Zorn H, Maison W. Green Chem. 2012; 14: 639
- 228 Krings U, Lehnert N, Fraatz MA, Hardebusch B, Zorn H, Berger RG. J. Agric. Food Chem. 2009; 57: 9944
- 229 Krügener S, Krings U, Zorn H, Berger RG. Bioresour. Technol. 2010; 101: 457
- 230 Fraatz MA, Riemer SJ. L, Stober R, Kaspera R, Nimtz M, Berger RG, Zorn H. J. Mol. Catal. B: Enzym. 2009; 61: 202
- 231 Zelena K, Krings U, Berger RG. Bioresour. Technol. 2012; 108: 231
- 232 Eskola J, Laakso S. Biochim. Biophys. Acta 1983; 751: 305
- 233 Brash AR, Ingram CD, Harris TM. Biochemistry 1987; 26: 5465
- 234 Clapp CH, Senchak SE, Stover TJ, Potter TC, Findeis PM, Novak MJ. J. Am. Chem. Soc. 2001; 123: 747