Metal-catalyzed asymmetric sulfoxidation, epoxidation and hydroxylation by hydrogen peroxide

Coordination Chemistry Reviews

Volumn 257, Issue 21-22, 2013, Pages 3030-3050

  Srour, Hassan ^a   Le Maux, Paul ^a   Chevance, Soizic ^a   Simonneaux, Gérard ^a  

^a INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

Author keywords

Asymmetric dihydroxylation; Asymmetric epoxidation; Asymmetric sulfoxidation; Hydrogen peroxide; Metal complex; Metalloporphyrin

Indexed keywords

EID: 84882774365     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2013.05.010     Document Type: Review

References (214)

1. Lane B.S., Burgess K. Chem. Rev. 2003, 103:2457.
2. Liao S., Coric I., Wang Q.L.B. J. Am. Chem. Soc. 2012, 134:10765.
3. Noyori R., Aoki M., Sato K. Chem. Commun. 2003, 1977.
4. Meunier B. Chem. Rev. 1992, 92:1411.
5. Arends I.W.C.E. Angew. Chem. Int. Ed. Engl. 2006, 45:6250.
6. Juliá S., Masana J., Vega J.C. Angew. Chem. Int. Ed. Engl. 1980, 19:929.
7. Zhuang W., Marigo M., Jorgensen K.A. Org. Biomol. Chem. 2005, 3:3883.
8. Russo A., De Fusco C., Lattanzi A. ChemCatChem 2012, 4:901.
9. ten Brink G.J., Arends I.W.C.E., Sheldon R.A. Chem. Rev. 2004, 104:4105.
10. Gusso A., Baccin C., Pinna F., Strukul G. Organometallics 1994, 13:3442.
11. Bianchini G., Cavarzan A., Scarzo A., Strukul G. Green Chem. 2009, 11:1517.
12. Cavarzan A., Bianchini G., Sgarbossa P., Lefort L., Gladiali S., Scarzo A., Strukul G. Chem. Eur. J. 2009, 15:7930.
13. Strukul G. Angew. Chem. Int. Ed. Engl. 1998, 37:1198.
14. Rentz M., Meunier B. Eur. J. Org. Chem. 1999, 737.
15. Pitchen P., Dunach E., Deshmukh M.N., Kagan H.B. J. Am. Chem. Soc. 1984, 106:8188.
16. Di Furia F., Modena G., Seraglia R. Synthesis 1984, 4:325.
17. Kaczorowska K., Kolarska Z., Mitka K., Kowalski P. Tetrahedron 2005, 61:8315.
18. Legros J., Dehli J.R., Bolm C. Adv. Synth. Catal. 2005, 347:19.
19. Fernandez I., Khiar N. Chem. Rev. 2003, 103:3651.
20. Kagan H.B. Organosulfur Chemistry in Asymmetric Synthesis 2008, 1. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. T. Toru, C. Bolm (Eds.).
21. Carreno M.C., Hernandez-Torres G., Rbagorda M., Urbano A. Chem. Commun. 2009, 6129.
22. O'Mahony G.E., Kelly P., Lawrence S.E., Maguire A.R. Arkivoc (i) 2011, 1.
23. Katsuki T. Pharmaceutical Process Chemistry 2011, 59. WILEY-VCH Verlag GmbH & Co., Weinheim, Germany. T. Shiori, I. Kunisuke, T. Konoike (Eds.).
24. Legros J., Bolm C. Angew. Chem. Int. Ed. Engl. 2004, 43:4225.
25. Legros J., Bolm C. Chem. Eur. J. 2005, 11:1086.
26. Egami H., Katsuki T. J. Am. Chem. Soc. 2007, 129:8940.
27. Duboc-Toia C., Menage S., Lambeaux C., Fontecave M. Tetrahedron Lett. 1997, 38:3727.
28. Duboc-Toia C., Menage S., Ho R.Y.N., Que L., Lambeaux C., Fontecave M. Inorg. Chem. 1999, 38:1261.
29. Mekmouche Y., Hummel H., Ho R.Y.N., Que J., Schünemannn L.V., Thomas F., Trautwein A.X., Lebrun C., Gorgy K., Leprêtre J.C., Collomb M.N., Deronzier A., Fontecave M., Menage S. Chem. Eur. J. 2002, 8:1196.
30. Legros J., Bolm C. Angew. Chem. Int. Ed. Engl. 2003, 115:5645.
31. Korte A., Legros J., Bolm C. Synlett 2004, 2397.
32. Egami H., Katsuki T. Synlett 2008, 10:1543.
33. Stingl K.A., Weiß K.M., Tsogoeva S.B. Tetrahedron 2012, 68:8493.
34. Simonneaux G., Tagliatesta P. J. Porph. Phtalocyan. 2004, 8:1166.
35. Oae S., Watanabe Y., Fujimori K. Tetrahedron Lett. 1982, 23:1189.
36. Colonna S., Gaggero N., Carrea G., Pasta P. J. Chem. Soc. Chem. Commun. 1992, 357.
37. Harris R.Z., Newmyer S.L., Ortiz de Montellano P.R. J. Biol. Chem. 1993, 268:1637.
38. van Deurzen M.P.J., van Rantwijk F., Sheldon R.A. Tetrahedron 1997, 53:13183.
39. Kadnikova E.N., Kostic N.M. J. Org. Chem. 2003, 68:2600.
40. Suzumura A., Paul D., Sugimoto H., Shinoda S., Julian R.R., Beauchamp J.L., Teraoka J., Tsukube H. Inorg. Chem. 2005, 44:904.
41. van de Velde F., Arends I.W.C.E., Sheldon R.A. J. Inorg. Biochem. 2000, 80:81.
42. Groves J.T., Viski P. J. Org. Chem. 1990, 55:3628.
43. Naruta Y., Tani F., Maruyama K. J. Chem. Soc. Chem. Commun. 1990, 1378.
44. Naruta Y., Tani F., Maruyama K. Tetrahedron: Asymmetry 1991, 2:533.
45. Chiang L.C., Konishi K., Aida T., Inoue S. J. Chem. Soc. Chem. Commun. 1992, 254.
46. Inoue S., Aida T., Konoshi K. J. Mol. Catal. A: Chem. 1992, 74:121.
47. Ferrand Y., Daviaud R., Le Maux P., Simonneaux G. Tetrahedron: Asymmetry 2006, 17:952.
48. Nam W., Han H.J., Oh S.-Y., Lee Y.J., Choi M.-H., Han S.-Y., Kim C., Woo S.K., Shin W. J. Am. Chem. Soc. 2000, 122:8677.
49. Baciocchi E., Gerini M.F., Lanzalunga O., Lapi A., Grazia Lo Piparo M. Org. Biomol. Chem. 2003, 1:422.
50. Wolak M., van Eldik R. Chem. Eur. J. 2007, 13:4873.
51. Le Maux P., Simonneaux G. Chem. Commun. 2011, 47:6957.
52. Lente G., Fabian I. Dalton Trans. 2007, 4268.
53. Hamelin O., Menage S., Charnay F., Chavarot M., Pierre J.-L., Pecaut J., Fontecave M. Inorg. Chem. 2008, 47:6413.
54. Arends I.W.C.E., Kodama T., Sheldon R.A. Topics in Organometallic Chemistry 11, Ruthenium Catalysts and Fine Chemistry 2004, vol. 11:277. Springer-Verlag, Berlin/Heidelberg.
55. Chavarot M., Menage S., Hamelin O., Charnay F., Pecaut J., Fontecave M. Inorg. Chem. 2003, 42:4810.
56. Palucki M., Hanson P., Jacobsen E.N. Tetrahedron Lett. 1992, 33:7111.
57. Schoumacker S., Hamelin O., Pecaut J., Fontecave M. Inorg. Chem. 2003, 42:8110.
58. Brinksma J., La Crois R., Feringa B.L., Donnoli M.I., Rosini C. Tetrahedron Lett. 2001, 42:4049.
59. Zhang Z., Guan F., Huang X., Wang Y., Sun Y. J. Mol. Catal. A: Chem. 2012, 364:343.
60. Carey J.R., Ma S.K., Pfister T.D., Garner D.K., Kim H.K., Abramite J.A., Wang Z., Guo Z., Lu Y. J. Am. Chem. Soc. 2004, 126:10812.
61. Zhang J.-L., Garner D.K., Liang L., Chen Q., Lu Y. Chem. Commun. 2008, 1665.
62. Zhang J.-L., Garner D.K., Liang L., Barrios D.A., Lu Y. Chem. -Eur. J. 2009, 15:7481.
63. Marques A., Marin M., Ruasse M.F. J. Org. Chem. 2001, 66:7588.
64. Srour H., Jalkh J., Le Maux P., Chevance S., Kobeissi M., Simonneaux G. J. Mol. Catal. A: Chem. 2013, 370:75.
65. Nigel-Etinger I., Mahammed A., Gross Z. Catal. Sci. Technol. 2011, 1:578.
66. Mahammed A., Gross Z. J. Am. Chem. Soc. 2005, 127:2883.
67. Yoshinaga K., Itoh N., Kito T. Polym. J. 1991, 23:65.
68. Bolm C. Coord. Chem. Rev. 2003, 237:245.
69. Volcho K.P., Salakhutdinov N.F. Russ. Chem. Rev. 2009, 78:457.
70. Bolm C., Bienewald F. Angew. Chem. Int. Ed. Engl. 1995, 34:2640.
71. Vetter A.H., Berkessel A. Tetrahedron Lett. 1998, 39:1741.
72. Ohta C., Shimizu H., Kondo A., Katsuki T. Synlett 2002, 1:161.
73. Pelotier B., Anson M.S., Campbell I.B., Macdonald S.J.F., Priem G., Jackson R.F.W.K. Synlett 2002, 7:1055.
74. Jeong Y.-C., Choi S., Hwang Y.D., Ahn K.-H. Tetrahedron Lett. 2004, 45:9249.
75. Plitt P., Pritzkow H., Oeser T., Kraemer R. J. Inorg. Biochem. 2005, 99:1230.
76. Gao A., Wang M., Wang D., Zhang L., Liu H., Tian W., Sun L. Chin. J. Catal. 2006, 27:743.
77. Liu H., Wang M., Wang Y., Yin R., Tian W., Sun L. Appl. Organomet. Chem. 2008, 22:253.
78. Wang Y., Wang M., Wang Y., Wang X., Wang L., Sun L. J. Catal. 2010, 273:177.
79. Ashikhmina E.V., Rubtsova S.A., Dvornikova I.A., Kuchin A.V. Russ. J. Org. Chem. 2009, 45:1509.
80. Karpyshev N.N., Yakovleva O.D., Talsi E.P., Bryliakov K.P., Tolstikova O.V., Tolstikov A.G. J. Mol. Catal. A: Chem. 2000, 157:91.
81. Sun J., Zhu C., Dai Z., Yang M., Pan Y., Hu H. J. Org. Chem. 2004, 69:8500.
82. Zeng Q., Wang H., Wang T., Cai Y., Weng W., Zhao Y. Adv. Synth. Catal. 2005, 347:1933.
83. Drago C., Caggiano L., Jackson R.F.W. Angew. Chem. Int. Ed. Engl. 2005, 44:7221.
84. Liu G., Cogan D.A., Ellman J.A. J. Am. Chem. Soc. 1997, 119:9913.
85. Cogan D.A., Liu G., Kim K., Backes B.J., Ellman J.A. J. Am. Chem. Soc. 1998, 120:8011.
86. Skarzewski J., Ostrycharz E.b., Siedlecka R. Tetrahedron: Asymmetry 1999, 10:3457.
87. Blum S.A., Bergman R.G., Ellman J.A. J. Org. Chem. 2002, 68:150.
88. Hartung J., Drees S., Greb M., Schmidt P., Svoboda I., Fuess H., Murso A., Stalke D. Eur. J. Org. Chem. 2003, 2003:2388.
89. Hsieh S.-H., Kuo Y.-P., Gau H.-M. Dalton Trans. 2007, 97.
90. Romanowski G., Lis T. Inorg. Chim. Acta 2013, 394:627.
91. Miyazaki T., Katsuki T. Synlett 2003, 7:1046.
92. Saito B., Katsuki T. Tetrahedron Lett. 2001, 42:3873.
93. Saito B., Katsuki T. Tetrahedron Lett. 2001, 42:8333.
94. Tanaka T., Saito B., Katsuki T. Tetrahedron Lett. 2002, 43:3259.
95. Saito B., Katsuki T. Chirality 2003, 15:24.
96. Bryliakov K.P., Talsi E.P. J. Mol. Catal. A: Chem. 2007, 264:280.
97. Bryliakov K.P., Talsi E.P. Eur. J. Org. Chem. 2008, 3369.
98. Blumenthal H., Liebscher J. Arkivoc (xi) 2009, 204.
99. Bryliakov K.P., Talsi E.P. Eur. J. Org. Chem. 2011, 2011:4693.
100. Talsi E.P., Bryliakov K.P. Appl. Organomet. Chem. 2013, 27:239.
101. Barman S., Patil S., Levy C.J. Chem. Lett. 2012, 41:974.
102. Adão P., Avecilla F., Bonchio M., Carraro M., Costa Pessoa J., Correia I. Eur. J. Inorg. Chem. 2010, 2010:5568.
103. Bera P.K., Ghosh D., Abdi S.H.R., Khan N.H., Kureshy R.I., Bajaj H.C. J. Mol. Catal. A: Chem. 2012, 361-362:36.
104. Scarso A., Strukul G. Adv. Synth. Catal. 2005, 347:1227.
105. Zhu H.-B., Dai Z.-Y., Huang W., Cui K., Gou S.-H., Zhu C.-J. Polyhedron 2004, 23:1131.
106. Kelly P., Lawrence S.E., Maguire A.R. Synlett 2007, 1501.
107. O'Mahony G.E., Ford A., Maguire A.R. J. Org. Chem. 2012, 77:3288.
108. Yamaguchi T., Matsumoto K., Saito B., Katsuki T. Angew. Chem. Int. Ed. Engl. 2007, 46:4729.
109. Matsumoto K., Yamaguchi T., Fujisaki J., Saito B., Katsuki T. Chem. Asian J. 2008, 3:351.
110. Matsumoto K., Yamaguchi T., Katsuki T. Chem. Commun. 2008, 1704.
111. Fujisaki J., Matsumoto K., Matsumoto K., Katsuki T. J. Am. Chem. Soc. 2011, 133:56.
112. Thakur V.V., Sudalai A. Tetrahedron: Asymmetry 2003, 14:407.
113. Zhang Y., Sun J.T., Zhu C.J. Chin. Chem. Lett. 2006, 17:1173.
114. Carraro M., Modugno G., Sartorel A., Scorrano G., Bonchio M. Eur. J. Inorg. Chem. 2009, 2009:5164.
115. Xia Q.H., Ge H.Q., Ye C.P., Liu Z.M., Su K.X. Chem. Rev. 2005, 105:1603.
116. De Faveri G., Ilyashenko G., Watkinson M. Chem. Soc. Rev. 2011, 40:1722.
117. Francis M.B., Jacobsen E.N. Angew. Chem. Int. Ed. Engl. 1999, 38:937.
118. Katsuki T., Sharpless K.B. J. Am. Chem. Soc. 1980, 102:5974.
119. Bolm C., Beckmann O., Kühn T., Palazzi C., Adam W., Rao P.B., Saha-Möller C.R. Tetrahedron: Asymmetry 2001, 12:2441.
120. Meunier D., Piechaczyk A., de Mallmann A., Basset J.-M. Angew. Chem. Int. Ed. Engl. 1999, 38:3540.
121. Zhang W., Basak A., Kosugi Y., Hoshino Y., Yamamoto H. Angew. Chem. Int. Ed. Engl. 2005, 44:4389.
122. Bourhani Z., Malkov A.V. Chem. Commun. 2005, 4592.
123. Egami H., Katsuki T. Angew. Chem. Int. Ed. Engl. 2008, 47:5171.
124. Egami H., Oguma T., Katsuki T. J. Am. Chem. Soc. 2010, 132:5886.
125. Talsi E.P., Bryliakov K.P. Coord. Chem. Rev. 2012, 256:1418.
126. Mansuy D. Comp. Biochem. Physiol. 1998, 121C:5.
127. Meunier B., de Visser S.P., Shaik S. Chem. Rev. 2004, 104:3947.
128. Rose E., Andrioletti B., Zrig S., Quelquejeu-Etheve M. Chem. Soc. Rev. 2005, 34:573.
129. White M.C., Doyle A.G., Jacobsen E.N. J. Am. Chem. Soc. 2001, 123:7194.
130. Gelalcha F.G., Bitterlich B., Anilkumar G., Tse M.K., Beller M. Angew. Chem. Int. Ed. Engl. 2007, 46:7293.
131. Gelalcha F.G., Anilkumar G., Tse M.K., Brückner A., Beller M. Chem. Eur. J. 2008, 14:7687.
132. Lyakin O.Y., Ottenbacher R.V., Bryliakov K.P., Talsi E.P. ACS Catal. 2012, 2:1196.
133. Wu M., Miao C.-X., Wang S., Hu X., Xia C., Kühn F.E., Sun W. Adv. Synth. Catal. 2011, 353:3014.
134. Ortiz de Montellano P.R.E. Cytochrome P-450: Structure, Mechanism and Biochemistry 1995, Plenum Press, New York. 2nd ed.
135. Joo H., Lin Z., Arnold F.H. Nature 1999, 399:670.
136. Cirino P.C., Arnold F.H. Adv. Synth. Catal. 2002, 344:932.
137. Fujishiro T., Shoji O., Nagano S., Sugimoto H., Shiro Y., Watanabe Y. J. Biol. Chem. 2011, 286:29941.
138. Shoji O., Watanabe Y. Metallomics 2011, 3:379.
139. Che C.M., Huang J.S. Chem. Commun. 2009, 3996.
140. Groves J.T., Nemo T.E., Myers R.S. J. Am. Chem. Soc. 1979, 101:1032.
141. Groves J.T., Myers R.S. J. Am. Chem. Soc. 1983, 105:5791.
142. Boitrel B., Lecas A., Renko Z., Rose E. J. Chem. Soc. Chem. Commun. 1985, 1820.
143. Mansuy D., Battioni P., Renaud J.P., Guerin P. J. Chem. Soc. Chem. Commun. 1985, 155.
144. Boitrel B., Lecas A., Renko Z., Rose E. New J. Chem. 1989, 13:73.
145. Collman J.P., Zhang X., Lee V.J., Uffelman E.S., Brauman J.I. Science 1993, 261:1404.
146. Gross Z., Ini S. J. Org. Chem. 1997, 62:5514.
147. Naruta Y., Tani F., Ishihara N., Maruyama K. J. Am. Chem. Soc. 1991, 113:6865.
148. Yang S.J., Nam W. Inorg. Chem. 1998, 37:606.
149. Stephenson N.A., Bell A.T. J. Am. Chem. Soc. 2005, 127:8635.
150. Le Maux P., Srour H., Simonneaux G. Tetrahedron 2012, 68:5824.
151. Stoop R.M., Mezzetti A. Green Chem. 1999, 1:39.
152. Stoop R.M., Bachmann S., Valentini M., Mezzetti A. Organometallics 2000, 19:4117.
153. Tse M.K., Dobler C., Bhor S., Klawonn M., Magerlein W., Hugl H., Beller M. Angew. Chem. Int. Ed. Engl. 2004, 43:5255.
154. Nishiyama H., Shimada T., Aoki K., Itoh H., Sugiyama H., Motoyama Y. Chem. Commun. 1997, 1863.
155. Tse M.K., Klawonn M., Bhor S., Dobler C., Anilkumar G., Hugl H., Magerlein W., Beller M. Org. Lett. 2005, 987.
156. Bhor S., Anilkumar G., Tse M.K., Klawonn M., Dobler C., Bitterlich B., Grotevendt A., Beller M. Org. Lett. 2005, 7:3393.
157. Zhang W., Loebach J.L., Wilson S.R., Jacobsen E.N. J. Am. Chem. Soc. 1990, 112:2801.
158. Jacobsen E.N., Zhang W., Muci A.R., Ecker J.R., Deng L. J. Am. Chem. Soc. 1991, 113:7063.
159. Palucki M., Pospisil P.J., Zhang W., Jacobsen E.N. J. Am. Chem. Soc. 1994, 116:9333.
160. Irie R., Noda K., Ito Y., Matsumoto N., Katsuki T. Tetrahedron Lett. 1990, 31:7345.
161. Irie R., Noda K., Ito Y., Matsumoto N., Katsuki T. Tetrahedron: Asymmetry 1991, 2:481.
162. Irie R., Hosoya N., Katsuki T. Synlett 1994, 255.
163. Pietikainen P. Tetrahedron Lett. 1994, 35:941.
164. Schwenkreis T., Berkessel A. Tetrahedron Lett. 1993, 34:4785.
165. Berkessel A., Frauenkron M., Schwenkreis T., Steinmetz A., Baum G., Fenske D. J. Mol. Catal. A: Chem. 1996, 113:321.
166. Bolm C., Kadereit D., Valacchi M. Synlett 1997, 687.
167. Romakh V.B., Therrien B., Suss-Fink G., Shulpin G.B. Inorg. Chem. 2007, 46:1315.
168. Wu M., Wang B., Wang S., Xia C., Sun W. Org. Lett. 2009, 11:3622.
169. Teixeira J., Silva A.R., Branco L.C., Afonso C.A.M., Freire C. Inorg. Chim. Acta 2010, 363:3321.
170. Ottenbacher R.V., Bryliakov K.P., Talsi E.P. Adv. Synth. Catal. 2011, 353:885.
171. Maity N.C., Rao G.V.S., Prathap K.J., Abdi S.H.R., Kureshy R.I., Khan N.-u.H., Bajaj H.C. J. Mol. Catal. A: Chem. 2013, 366:380.
172. Vilain S., Maillard P., Momenteau M. J. Chem. Soc. Chem. Commun. 1994, 1697.
173. Vilain-Deshayes S., Robert A., Maillard P., Meunier B., Momenteau M. J. Mol. Catal. A: Chem. 1996, 113:23.
174. Collman J.P., Lee V.J., Kellen-Yuen C.J., Zang X., Ibers J.A., Brauman J.I. J. Am. Chem. Soc. 1995, 117:692.
175. Srour H., Le Maux P., Simonneaux G. Inorg. Chem. 2012, 51:5850.
176. Chatel G., Goux-Henry C., Mirabaud A.s., Rossi T., Kardos N., Andrioletti B., Draye M. J. Catal. 2012, 291:127.
177. Chu Y., Liu X., Li W., Hu X., Lin L., Feng X. Chem. Sci. 2012, 3:1996.
178. Matsumoto K., Sawada Y., Saito B., Sakai K., Katsuki T. Angew. Chem. Int. Ed. Engl. 2005, 44:4935.
179. Sawada Y., Matsumoto K., Katsuki T. Angew. Chem. Int. Ed. Engl. 2007, 46:4559.
180. Sawada Y., Matsumoto K., Kondo S., Watanabe H., Ozawa T., Suzuki K., Saito B., Katsuki T. Angew. Chem. Int. Ed. Engl. 2006, 45:3478.
181. Matsumoto K., Sawada Y., Katsuki T. Pure Appl. Chem. Commun. 2008, 80:1071.
182. Matsumoto K., Feng C., Handa S., Oguma T., Katsuki T. Tetrahedron 2011, 67:6474.
183. Sinigalia R., Michelin R.A., Pinna F., Strukul G. Organometallics 1987, 6:728.
184. Colladon M., Scarso A., Strukula G. Adv. Synth. Catal. 2007, 797.
185. Prasetyanto A.E., Khan N.H., Seo H.U., Park S.E. Top. Catal. 2010, 53:1381.
186. Herrmann W.A., Kahn F.E. Acc. Chem. Res. 1997, 30:169.
187. Romao C.C., Kahn F.E., Herrmann W.A. Chem. Rev. 1997, 97:3197.
188. Kahn F.E., Zhao J., Herrmann W.A. Tetrahedron: Asymmetry 2005, 16:3469.
189. Sabater M.Ì.J., Domine M.E., Corma A. J. Catal. 2002, 210:192.
190. Haider J.J., Kratzer R.M., Herrmann W.A., Zhao J., Kahn F.E. J. Organomet. Chem. 2004, 689:3735.
191. Li S., Zhang B., Kühn F.E. J. Organomet. Chem. 2013, 730:132.
192. Wang Z.-M., Kakiuchi K., Sharpless K.B. J. Org. Chem. 1994, 59:6895.
193. Kolb H.C., VanNieuwenhze M.S., Sharpless K.B. Chem. Rev. 1994, 94:2483.
194. Balagam B., Mitra R., Richardson D.E. Tetrahedron Lett. 2008, 49:1071.
195. Jonsson S.Y., Färnegardh K., Bäckvall J.-E. J. Am. Chem. Soc. 2001, 123:1365.
196. Costas M., Tipton A.K., Chen K., Jo D.-H., Que L. J. Am. Chem. Soc. 2001, 123:6722.
197. Suzuki K., Oldenburg P.D., Que J.L. Angew. Chem. Int. Ed. Engl. 2008, 47:1887.
198. de Boer J.W., Browne W.R., Brinksma J., Alsters P.L., Hage R., Feringa B.L. Inorg. Chem. 2007, 46:6353.
199. de Boer J.W., Browne W.R., Harutyunyan S.R., Bini L., Tiemersma-Wegman T.D., Alsters P.L., Hage R., Feringa B.L. Chem. Commun. 2008, 3747.
200. Saisaha P., de Boer J.W., Browne W.R. Chem. Soc. Rev. 2013, 42:2059.
201. Choudary B.M., Chowdari N.S., Madhi S., Kantam M.L. J. Org. Chem. 2003, 68:1736.
202. Sugimoto H., Kitayama K., Mori S., Itoh S. J. Am. Chem. Soc. 2012, 134:19270.
203. Borovik A.S. Chem. Soc. Rev. 2011, 40:1870.
204. Che C.M., Lo V.K.Y., Zhou C.Y., Huang J.S. Chem. Soc. Rev. 2011, 40:1950.
205. Lu H., Zhang X.P. Chem. Soc. Rev. 2011, 40:1899.
206. Ortiz de Montellano P.R. Chem. Rev. 2009, 110:932.
207. Kinne M., Poraj-Kobielska M.R., Ullrich S.A.R., Hofrichter M., Hammel K.E. J. Biol. Chem. 2009, 284:29343.
208. Wang X., Peter S., Kinne M., Hofrichter M., Groves J.T. J. Am. Chem. Soc. 2012, 134:12897.
209. Mekmouche Y., Duboc-Toia C., Menage S., Lambeaux C., Fontecave M. J. Mol. Catal. A: Chem. 2000, 156:85.
210. Groves J.T., Viski P. J. Am. Chem. Soc. 1989, 111:8537.
211. Gross Z., Ini S. Org. Lett. 1999, 1:2077.
212. Zhang R., Yu W.-Y., Lai T.-S., Che C.-M. Chem. Commun. 1999, 1791.
213. Zhang R., Yu W.-Y., Che C.-M. Tetrahedron: Asymmetry 2005, 16:3520.
214. Simonneaux G., Le Maux P., Ferrand Y., Rault-Berthelot J. Coord. Chem. Rev. 2006, 250:2212.