Oxidation Adjacent to C X Bonds by Dehydrogenation

Comprehensive Organic Synthesis: Second Edition

Volumn 7, Issue , 2014, Pages 178-212

  Stahl, S S ^a   Diao, T ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Aerobic; Carbonyl Compounds; Dehydrogenation; Enone; Hypervalent iodine; Pd catalysis; , Unsaturation

Indexed keywords

BIOACTIVITY; CATALYSIS; CONDENSATION REACTIONS; DEHYDROGENATION; OXIDATION; REAGENTS; UNSATURATED COMPOUNDS;

AEROBIC; BIOLOGICALLY ACTIVE COMPOUNDS; CATALYTIC DEHYDROGENATION; DEHYDROGENATION REACTIONS; ENONE; HYPERVALENT IODINE; HYPERVALENT IODINE REAGENTS; UNSATURATED CARBONYL COMPOUNDS;

CARBONYL COMPOUNDS;

EID: 84903491408     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-08-097742-3.00707-2     Document Type: Chapter

References (236)

1. Patai S., Rappoport Z. The Chemistry of Enones 1989, John Wiley & Sons Ltd, New York.
2. Buckle D.R., Pinto I.L. Oxidation Adjacent to CX Bonds by Dehydrogenation. Comprehensive Organic Synthesis - Selectivity, Strategy and Efficiency in Modern Organic Chemistry 1991, Vol. 7:119-149. Pergamon Press, Oxford.
3. For a summary of pKa data, see: http://www.chem.wisc.edu/areas/reich/pkatable/.
4. Lange G.L., Organ M.G., Roche M.R. J. Org. Chem. 1992, 57:6000-6002.
5. Zimmermann J., Seebach D. Helv. Chim. Acta 1987, 70:1104-1114.
6. Jones G. J. Chem. Soc. C 1970, 1230-1232.
7. Miller D.D., Moorthy K.B., Hamada A. Tetrahedron Lett. 1983, 24:555-556.
8. Goud P.M., Sheri A., Desai P.V., et al. Med. Chem. Res. 2005, 14:74-105.
9. Palmer C.J., Josephs J.L. J. Chem. Soc. Perkin Trans. 1 1995, 3135-3152.
10. Horiuchi C.A., Kiji S. Chem. Lett. 1988, 17:31-34.
11. House H. Modern Synthetic Reactions 1972, W. A. Benjamin Inc., Menlo Park, CA. 2nd ed.
12. Calo V., Lopez L., Pesce G. J. Chem. Soc. Perkin Trans. 1 1977, 501-504.
13. Stotter P.L., Hill K.A. J. Org. Chem. 1973, 38:2576-2578.
14. d'Angelo J. Tetrahedron 1976, 32:2979-2990.
15. Reuss R.H., Hassner A. J. Org. Chem. 1974, 39:1785-1787.
16. Blanco L., Amice P., Conia J.M. Synthesis 1976, 1976:194-196.
17. Cambie R.C., Hayward R.C., Jurlina J.L., Rutledge P.S., Woodgate P.D. J. Chem. Soc. Perkin Trans. 1 1978, 126-130.
18. Ladjama D., Rieel J.J. Synthesis 1979, 1979:504-507.
19. Krebs A., Swienty-Busch J. Eliminations to Form Alkenes, Allenes and Alkynes and Related Reactions. Comprehensive Organic Synthesis - Selectivity, Strategy and Efficiency in Modern Organic Chemistry 1991, Vol. 6:950-973. Pergamon Press, Oxford.
20. Zhang F., Song Z.J., Tschaen D., Volante R.P. Org. Lett. 2004, 6:3775-3777.
21. Bellamy F.D., Chazan J.B., Ou K. Tetrahedron 1983, 39:2803-2806.
22. Rathke M.W., Lindert A. Tetrahedron Lett. 1971, 12:3995-3998.
23. Singer S.P., Sharpless K.B. J. Org. Chem. 1978, 43:1448-1455.
24. Greene A.E., Muller J.C., Ourisson G. Tetrahedron Lett. 1972, 13:2489-2492.
25. Greene A.E., Muller J.C., Ourisson G. J. Org. Chem. 1974, 39:186-191.
26. Da Costa R., Gillard M., Falmagne J.B., Ghosez L. J. Am. Chem. Soc. 1979, 101:4381-4383.
27. Williams D.R., Lowder P.D., Gu Y.-G., Brooks D.A. Tetrahedron Lett. 1997, 38:331-334.
28. Brown R.S., Dowden J., Moreau C., Potter B.V.L. Tetrahedron Lett. 2002, (43):6561-6562.
29. Mislin G.L., Burger A., Abdallah M.A. Tetrahedron 2004, 60:12139-12145.
30. Phillips A.J., Uto Y., Wipf P., Reno M.J., Williams D.R. Org. Lett. 2000, 2:1165-1168.
31. Sofiyev V., Lumb J.-P., Volgraf M., Trauner D. Chem. Eur. J. 2012, 18:4999-5005.
32. Nakatsuka M., Nakasuji K., Murata I., et al. Chem. Lett. 1983, 12:905-908.
33. Trost B.M., Salzmann T.N., Hiroi K. J. Am. Chem. Soc. 1976, 98:4887-4902.
34. Trost B.M. Chem. Rev. 1978, 78:363-382.
35. Seebach D., Teschner M. Chem. Ber. 1976, 109:1601-1616.
36. Braslau R. Dimethyl Disulfide. e-EROS Encyclopedia of Reagents for Organic Synthesis 2001, John Wiley & Sons, Ltd, New York, DOI: 10.1002/047084289X.rd331. D. Crich (Ed.).
37. Byers J.H Diphenyl Disulfide. e-EROS Encyclopedia of Reagents for Organic Synthesis 2001, John Wiley & Sons, Ltd, New York, DOI: 10.1002/047084289X.rd415.
38. Coates R.M., Pigott H.D. Synthesis 1975, 1975:319-320.
39. Monteiro H.J., de Souza J.P. Tetrahedron Lett. 1975, 16:921-924.
40. Trost B.M., Parquette J.R. J. Org. Chem. 1993, 58:1579-1581.
41. Kingsbury C.A., Cram D.J. J. Am. Chem. Soc. 1960, 82:1810-1819.
42. Matsuo J.-i., Iida D., Tatani K., Mukaiyama T. Bull. Chem. Soc. Jpn. 2002, 75:223-234.
43. Mukaiyama T., Matsuo J.-i., Kitagawa H. Chem. Lett. 2000, 29:1250-1251.
44. Hara S., Makino K., Hamada Y. Tetrahedron 2004, 60:8031-8035.
45. Hamada Y., Kawai A., Kohno Y., Hara O., Shioiri T. J. Am. Chem. Soc. 1989, 111:1524-1525.
46. Cheng W.-C., Lin C.-C., Kurth M.J. Tetrahedron Lett. 2002, 43:2967-2970.
47. Chen Y., Lam Y., Lai Y.-H. Org. Lett. 2002, 4:3935-3937.
48. Reich H.J., Reich I.L., Renga J.M. J. Am. Chem. Soc. 1973, 95:5813-5815.
49. Sharpless K.B., Young M.W., Lauer R.F. Tetrahedron Lett. 1973, 14:1979-1982.
50. Sharpless K.B., Lauer R.F., Teranishi A.Y. J. Am. Chem. Soc. 1973, 95:6137-6139.
51. Clive D.L.J. Tetrahedron 1978, 34:1049-1132.
52. Jones D.N., Mundy D., Whitehou R.D. J. Chem. Soc. Chem. Comm. 1970, 86-87.
53. Macdougall P.E., Smith N.A., Schiesser C.H. Tetrahedron 2008, 64:2824-2831.
54. Reich H.J., Reich I.L., Renga J.M. J. Am. Chem. Soc. 1973, 95:5813-5815.
55. Reich H.J., Renga J.M., Reich I.L. J. Am. Chem. Soc. 1975, 97:5434-5447.
56. Reich H.J. Acc. Chem. Res. 1979, 12:22-30.
57. Sharpless K.B., Gordon K.M., Lauer R.F., et al. Chem. Scr. 1975, 8A:9-13.
58. Reich H.J. Organoselenium Oxidations. Oxidationin Organic Chemistry, Part C 1978, 1-130. Academic Press, New York. W. Trahanovsky (Ed.).
59. Back, T. G. Selenium: Organoselenium Chemistry. In Encyclopedia of Inorganic and Bioinorganic Chemistry; John Wiley & Sons, 2011.
60. Organoselenium Chemistry: A Practical Approach 1999, Oxford University Press, Oxford. T.G. Back (Ed.).
61. Wirth T. Organoselenium Chemistry: Modern Developments in Organic Synthesis 2000, Springer, Berlin, Vol. 208.
62. Raghavan S., Babu V.S. Tetrahedron 2011, 67:2044-2050.
63. McAllister L.A., McCormick R.A., Procter D.J. Tetrahedron 2005, 61:11527-11576.
64. Nicolaou K.C., Pastor J., Barluenga S., Winssinger N. Chem. Commun. 1998, 1947-1948.
65. Michels R., Kato M., Heitz W. Die Makromol. Chem. 1976, 177:2311-2320.
66. Hiroi K., Sato S. Synthesis 1985, 1985:635-638.
67. Komatsu N., Matsunaga S., Sugita T., Uemura S. J. Am. Chem. Soc. 1993, 115:5847-5848.
68. Krief A., Badaoui E., Dumont W., et al. Tetrahedron Lett. 1991, 32:3231-3234.
69. Peover M.E. J. Chem. Soc. 1962, 0:4540-4549.
70. Walker D., Hiebert J.D. Chem. Rev. 1967, 67:153-195.
71. Buckle D.R., Collier S.J., McLaws M.D. 2,3-Dichloro-5,6-dicyano-1,4-benzo-quinone. e-EROS Encyclopedia of Reagents for Organic Synthesis 2005, John Wiley & Sons, Inc., New York, DOI: 10.1002/047084289X.rd114.pub2. D. Crich (Ed.).
72. Buckle D.R. Chloranil. e-EROS Encyclopedia of Reagents for Organic Synthesis 2001, John Wiley & Sons, Inc., New York, DOI: 10.1002/047084289X.rc057. D. Crich (Ed.).
73. Braude E.A., Jackman L.M., Linstead R.P. J. Chem. Soc. 1954, 3548-3563.
74. Ringold H.J., Gut M., Hayano M., Turner A. Tetrahedron Lett. 1962, 3:835-837.
75. Ringold H.J., Turner A. Chem. Ind. 1962, 211-212.
76. Di Filippo M., Izzo I., Raimondi S., De Riccardis F., Sodano G. Tetrahedron Lett. 2001, 42:1575-1577.
77. Kondo T., Oyama K.-i., Yoshida K. Angew. Chem. Int. Ed. 2001, 40:894-897.
78. Huo C., Xu X., An J., et al. J. Org. Chem. 2012, 77:8310-8316.
79. Gupta A.K.D., Chatterje R.M., Paul M. J. Chem. Soc. C 1971, 3367-3370.
80. Bhattacharya A., DiMichele L.M., Dolling U.H., Douglas A.W., Grabowski E.J.J. J. Am. Chem. Soc. 1988, 110:3318-3319.
81. van Tamelen E.E., Hildahl G.T. J. Am. Chem. Soc. 1956, 78:4405-4412.
82. Fleming I., Paterson I. Synthesis (Stuttg) 1979, 736-738.
83. Hartman C., Meyer V. Chem. Ber. 1893, 26:1727.
84. Frigerio M., Santagostino M. Tetrahedron Lett. 1994, 35:8019-8022.
85. Corey E.J., Palani A. Tetrahedron Lett. 1995, 36:3485-3488.
86. Nicolaou K.C., Zhong Y.L., Baran P.S. J. Am. Chem. Soc. 2000, 122:7596-7597.
87. Duschek A., Kirsch S.F. Angew. Chem. Int. Ed. 2011, 50:1524-1552.
88. Silva J.L.F., Olofsson B. Nat. Prod. Rep. 2011, 28:1722-1754.
89. Lalic G., Corey E.J. Org. Lett. 2007, 9:4921-4923.
90. Nicolaou K.C., Stepan A.F., Lister T., et al. J. Am. Chem. Soc. 2008, 130:13110-13119.
91. Austin K.A.B., Banwell M.G., Willis A.C. Org. Lett. 2008, 10:4465-4468.
92. Dong S., Hamel E., Bai R., et al. Angew. Chem. Int. Ed. 2009, 48:1494-1497.
93. Frigerio M., Santagostino M., Sputore S. J. Org. Chem. 1999, 64:4537-4538.
94. Robert K., Boeckman J., Shao P., Mullins J.J. Org. Synth. 2000, 77:141-147.
95. Plumb J.B., Harper D.J. Chem. Eng. News 1990, 68:3.
96. Dess D.B., Martin J.C. J. Am. Chem. Soc. 1991, 113:7277-7287.
97. Nicolaou K.C., Montagnon T., Baran P.S., Zhong Y.L. J. Am. Chem. Soc. 2002, 124:2245-2258.
98. Fallis A.G., Tessier P.E. 2-Iodoxybenzoic Acid (IBX). e-EROS Encyclopedia of Reagents for Organic Synthesis 2003, John Wiley & Sons, Ltd., New York, DOI: 10.1002/047084289X.rn00221. D. Crich (Ed.).
99. Nicolaou K.C., Baran P.S., Kranich R., et al. Angew. Chem. Int. Ed. 2001, 40:202-206.
100. Dounay A.B., Humphreys P.G., Overman L.E., Wrobleski A.D. J. Am. Chem. Soc. 2008, 130:5368-5377.
101. Trost B.M., Zhang T. Chem. Eur. J. 2011, 17:3630-3643.
102. Movassaghi M., Hunt D.K., Tjandra M. J. Am. Chem. Soc. 2006, 128:8126-8127.
103. Yokoe H., Mitsuhashi C., Matsuoka Y., et al. J. Am. Chem. Soc. 2011, 133:8854-8857.
104. Zhang D.-H., Cai F., Zhou X.-D., Zhou W.-S. Org. Lett. 2003, 5:3257-3259.
105. Horner J.H., Newcomb M. J. Am. Chem. Soc. 2001, 123:4364-4365.
106. Nicolaou K.C., Montagnon T., Baran P.S. Angew. Chem. Int. Ed. 2002, 41:993-996.
107. Coleman R.S., Campbell E.L., Carper D.J. Org. Lett. 2009, 11:2133-2136.
108. Gallen M.J., Goumont R., Clark T., Terrier F., Williams C.M. Angew. Chem. Int. Ed. 2006, 45:2929-2934.
109. Heim R., Wiedemann S., Williams C.M., Bernhardt P.V. Org. Lett. 2005, 7:1327-1329.
110. Cui L.-Q., Dong Z.-L., Liu K., Zhang C. Org. Lett. 2011, 13:6488-6491.
111. Richardson R.D., Zayed J.M., Altermann S., Smith D., Wirth T. Angew. Chem. Int. Ed. 2007, 46:6529-6532.
112. Sorg G., Mengel A., Jung G., Rademann J. Angew. Chem. Int. Ed. 2001, 40:4395-4397.
113. Barontini M., Bernini R., Crisante F., Fabrizi G. Tetrahedron 2010, 66:6047-6053.
114. Uyanik M., Akakura M., Ishihara K. J. Am. Chem. Soc. 2009, 131:251-262.
115. Nicolaou K.C., Montagnon T., Baran P.S. Angew. Chem. Int. Ed. 2002, 41:1386-1389.
116. Boger D.L., Zhu Y. J. Org. Chem. 1994, 59:3453-3458.
117. Fukuoka M., Kuroyanagi M., Yoshihira K., Natori S. Chem. Pharm. Bull. 1978, 26:2365-2385.
118. Nicolaou K.C., Mathison C.J.N. Angew. Chem. Int. Ed. 2005, 44:5992-5997.
119. Nicolaou K.C., Gray D.L.F., Montagnon T., Harrison S.T. Angew. Chem. Int. Ed. 2002, 41:996-999.
120. Hiroya K., Suwa Y., Ichihashi Y., Inamoto K., Doi T. J. Org. Chem. 2011, 76:4522-4532.
121. Yoshimitsu T., Nojima S., Hashimoto M., Tanaka T. Org. Lett. 2011, 13:3698-3701.
122. Nicolaou K.C., Li A., Edmonds D.J., Tria G.S., Ellery S.P. J. Am. Chem. Soc. 2009, 131:16905-16918.
123. Hirai S., Nakada M. Tetrahedron 2011, 67:518-530.
124. Nicolaou K.C., Peng X.-S., Sun Y.-P., et al. J. Am. Chem. Soc. 2009, 131:10587-10597.
125. Cazeau P., Duboudin F., Moulines F., Babot O., Dunogues J. Tetrahedron 1987, 43:2075-2088.
126. Leahy E.M., Zhang W. Chlorotrimethylsilane. e-EROS Encyclopedia of Reagents for Organic Synthesis 2008, John Wiley & Sons, Inc., New York, DOI: 10.1002/047084289X.rc156.pub2. D. Crich (Ed.).
127. Hiraoka S., Harada S., Nishida A. J. Org. Chem. 2010, 75:3871-3874.
128. Kravetz T.M., Cheney D., Paquette L.A. Org. Synth. 1988, 66:43-48.
129. Muzart J. Eur. J. Org. Chem. 2010, 3779-3790.
130. Hartwig J. Organotransition Metal Chemistry: From Bonding to Catalysis 2010, University Science Books, Sausalito, pp 825-870.
131. Fuchita Y., Harada Y. Inorg. Chim. Acta 1993, 208:43-47.
132. Culkin D.A., Hartwig J.F. Acc. Chem. Res. 2003, 36:234-245.
133. Hartwig J. Organotransition Metal Chemistry: From Bonding to Catalysis 2010, University Science Books, Sausalito, pp 398-405.
134. Porth S., Bats J.W., Trauner D., Giester G., Mulzer J. Angew. Chem. Int. Ed. 1999, 38:2015-2016.
135. Baltz, H.; Bierling, B.; Kirschke, K.; Oberender, H.; Schulz, M.(VEB Leuna-Werke, Walter Ulbricht) α,β-Unsaturated Ketones from Saturated Ketones. Ger. Offen. DE2050566 (A1), 1971; Chem. Abstr.1971, 75, 19800.
136. Bierling B., Kirschke K., Oberender H., Schulz M. J. Prakt. Chem. 1972, 314:170-180.
137. Shan S. Jingxi Shiyou Huagong Jinzhan 2005, 6:24-25. Chem. Abstr. 146, 401642.
138. Kirschke K., Muller H., Timm D. J. Prakt. Chem. 1975, 317:807-811.
139. Mukaiyama T., Ohshima M., Nakatsuka T. Chem. Lett. 1983, 12:1207-1210.
140. Murahashi S.I., Mitsue Y., Tsumiyama T. Bull. Chem. Soc. Jpn. 1987, 60:3285-3290.
141. Theissen R.J. J. Org. Chem. 1971, 36:752-757.
142. Parker K.A., Koziski K.A., Breault G. Tetrahedron Lett. 1985, 26:2181-2182.
143. Greene A.E., Luche M.J., Depres J.P. J. Am. Chem. Soc. 1983, 105:2435-2439.
144. Greene A.E., Luche M.J., Serra A.A. J. Org. Chem. 1985, 50:3957-3962.
145. Trost B.M., Dong G., Vance J.A. Chem. Eur. J. 2010, 16:6265-6277.
146. Hanzawa Y., Ito H., Kohara N., et al. Tetrahedron Lett. 1991, 32:4143-4146.
147. Baltz, H.; Bierling, B.; Kirschke, K.; Oberender, H.; Schulz, M.(VEB Leuna-Werke, Walter Ulbricht) Process for the Production of α,β-Unsaturated Ketones. Brit. Pat. Appl. GB 1,340,612 (A), 1973; Chem. Abstr.1974, 80, 120393.
148. Susuki T., Tsuji J. Bull. Chem. Soc. Jpn. 1973, 46:655-656.
149. Shvo Y., Arisha A.H.I. J. Org. Chem. 1998, 63:5640-5642.
150. Guijarro D., Mancheño B., Yus M. Tetrahedron 1994, 50:8551-8558.
151. Giri R., Maugel N., Foxman B.M., Yu J.-Q. Organometallics 2008, 27:1667-1670.
152. Stahl S.S. Science 2005, 309:1824-1826.
153. Stahl S.S. Angew. Chem. Int. Ed. 2004, 43:3400-3420.
154. Shi Z., Zhang C., Tang C., Jiao N. Chem. Soc. Rev. 2012, 41:3381-3430.
155. Ye X.A., Johnson M.D., Diao T.N., Yates M.H., Stahl S.S. Green Chem. 2010, 12:1180-1186.
156. Wenzel T.T. J. Chem. Soc. Chem. Commun. 1989, 932-933.
157. Muzart J., Pete J.P. J. Mol. Catal. 1982, 15:373-376.
158. Park Y.W., Oh H.H. Bull. Korean Chem. Soc. 1997, 18:1123-1124.
159. Tokunaga M., Harada S., Iwasawa T., Obora Y., Tsuji Y. Tetrahedron Lett. 2007, 48:6860-6862.
160. Diao T.N., Stahl S.S. J. Am. Chem. Soc. 2011, 133:14566-14569.
161. Diao T., White P., Guzei I., Stahl S.S. Inorg. Chem. 2012, 51:11898-11909.
162. Izawa Y., Pun D., Stahl S.S. Science 2011, 333:209-213.
163. Zhu J., Liu J., Ma R.Q., et al. Adv. Synth. Catal. 2009, 351:1229-1232.
164. Liu J., Zhu J., Jiang H.L., Wang W., Li J. Chem. Asian J. 2009, 4:1712-1716.
165. Gao W., He Z., Qian Y., Zhao J., Huang Y. Chem. Sci. 2012, 3:883-886.
166. Diao T., Wadzinski T.J., Stahl S.S. Chem. Sci. 2012, 3:887-891.
167. Zhang F., Moher E.D., Zhang T.Y. Tetrahedron Lett. 2007, 48:3277-3279.
168. Leskinen M.V., Yip K.-T., Valkonen A., Pihko P.M. J. Am. Chem. Soc. 2012, 134:5750-5753.
169. Yip K.-T., Nimje R.Y., Leskinen M.V., Pihko P.M. Chem. Eur. J. 2012, 18:12590-12594.
170. Zhou J., Wu G., Zhang M., Jie X., Su W. Chem. Eur. J. 2012, 18:8032-8036.
171. Shang Y., Jie X., Zhou J., et al. Angew. Chem. Int. Ed. 2012, 1299-1303.
172. Moon Y., Kwon D., Hong S. Angew. Chem. Int. Ed. 2012, 51:11333-11336.
173. Girard S.A., Hu X., Knauber T., et al. Org. Lett. 2012, 14:5606-5609.
174. Hajra A., Wei Y., Yoshikai N. Org. Lett. 2012, 14:5488-5491.
175. Xie Y., Liu S., Liu Y., Wen Y., Deng G.-J. Org. Lett. 2012, 14:1692-1695.
176. Imahori T., Tokuda T., Taguchi T., Takahata H. Org. Lett. 2012, 14:1172-1175.
177. Simon M.-O., Girard S.A., Li C.-J. Angew. Chem. Int. Ed. 2012, 51:7537-7540.
178. Ito Y., Hirao T., Saegusa T. J. Org. Chem. 1978, 43:1011-1013.
179. Lauer M.G., Henderson W.H., Awad A., Stambuli J.P. Org. Lett. 2012, 14:6000-6003.
180. Larock R.C., Hightower T.R., Kraus G.A., Hahn P., Zheng D. Tetrahedron Lett. 1995, 36:2423-2426.
181. Kraus G.A., Zheng D. Synlett 1993, 1993:71-72.
182. Zierkiewicz W., Privalov T. Organometallics 2005, 24:6019-6028.
183. Steinhoff B.A., Stahl S.S. J. Am. Chem. Soc. 2006, 128:4348-4355.
184. Lu Y., Nguyen P.L., Lévaray N., Lebel H. J. Org. Chem. 2012, 78:776-779.
185. Fujioka K., Yokoe H., Yoshida M., Shishido K. Org. Lett. 2011, 14:244-247.
186. Hauser F.M., Zhou M.T., Sun Y.Q. Synth. Commun. 2001, 31:77-80.
187. Chen J.-Q., Xie J.-H., Bao D.-H., Liu S., Zhou Q.-L. Org. Lett. 2012, 14:2714-2717.
188. Liu J., Lotesta S.D., Sorensen E.J. Chem. Commun. 2011, 47:1500-1502.
189. Namba K., Kaihara Y., Yamamoto H., et al. Chem. Eur. J. 2009, 15:6560-6563.
190. Fuwa H., Kainuma N., Tachibana K., Sasaki M. J. Am. Chem. Soc. 2002, 124:14983-14992.
191. Marino J.P., Rubio M.B., Cao G., de Dios A. J. Am. Chem. Soc. 2002, 124:13398-13399.
192. Aoki K., Tomioka K., Noguchi H., Koga K. Tetrahedron 1997, 53:13641-13656.
193. Anderson J.D., García García P., Hayes D., et al. Tetrahedron Lett. 2001, 42:7111-7114.
194. Graf C.-D., Malan C., Knochel P. Angew. Chem. Int. Ed. 1998, 37:3014-3016.
195. Shirai R., Tanaka M., Koga K. J. Am. Chem. Soc. 1986, 108:543-545.
196. Clark J.S., Vignard D., Parkin A. Org. Lett. 2011, 13:3980-3983.
197. Rodeschini V., Vande Weghe P., Salomon E., Tarnus C., Eustache J. J. Org. Chem. 2005, 70:2409-2412.
198. Herzon S.B., Lu L., Woo C.M., Gholap S.L. J. Am. Chem. Soc. 2011, 133:7260-7263.
199. Tsuji J., Takahashi K., Minami I., Shimizu I. Tetrahedron Lett. 1984, 25:4783-4786.
200. Minami I., Takahashi K., Shimizu I., Kimura T., Tsuji J. Tetrahedron 1986, 42:2971-2977.
201. Yu J.-Q., Wu H.C., Corey E.J. Org. Lett. 2005, 7:1415-1417.
202. Barrish J.C., Singh J., Spergel S.H., et al. J. Org. Chem. 1993, 58:4494-4496.
203. Pihko P.M., Koskinen A.M.P. J. Org. Chem. 1998, 63:92-98.
204. Meyers A.I., Tavares F. Tetrahedron Lett. 1994, 35:2481-2484.
205. Meyers A.I., Tavares F.X. J. Org. Chem. 1996, 61:8207-8215.
206. Ramirez T.A., Zhao B., Shi Y. Tetrahedron Lett. 2010, 51:1822-1825.
207. Wang Y., Li Z., Huang Y., et al. Tetrahedron 2011, 67:7406-7411.
208. Dawsey A.C., Li V., Hamilton K.C., Wang J., Williams T.J. Dalton Trans. 2012, 41:7994-8002.
209. Evans D.L., Minster D.K., Jordis U., et al. J. Org. Chem. 1979, 44:497-501.
210. Shin C.-g., Nakamura Y., Okumura K. Chem. Lett. 1993, 22:1405-1408.
211. Hamada Y., Shibata M., Sugiura T., Kato S., Shioiri T. J. Org. Chem. 1987, 52:1252-1255.
212. Andrus M.B., Lashley J.C. Tetrahedron 2002, 58:845-866.
213. Huang Y., Gan H., Li S., et al. Tetrahedron Lett. 2010, 51:1751-1753.
214. Rao P.N., Cessac J.W., Kim H.K. Steroids 1994, 59:621-627.
215. Ushakov D.B., Raja A., Franke R., Sasse F., Maier M.E. Synlett 2012, 23:1358-1360.
216. Ueno S., Shimizu R., Kuwano R. Angew. Chem. Int. Ed. 2009, 48:4543-4545.
217. Moriuchi T., Kikushima K., Kajikawa T., Hirao T. Tetrahedron Lett. 2009, 50:7385-7387.
218. Flick A.C., Padwa A. Arkivoc 2011, 137-161.
219. Flick A.C., Padwa A. Tetrahedron Lett. 2008, 49:5739-5741.
220. Ley S.V., Norman J., Griffith W.P., Marsden S.P. Synthesis 1994, 1994:639-666.
221. Shimokawa J., Ishiwata T., Shirai K., et al. Chem. Eur. J. 2005, 11:6878-6888.
222. Dobereiner G.E., Crabtree R.H. Chem. Rev. 2010, 110:681-703.
223. Zhang X., Wang D.Y., Emge T.J., Goldman A.S. Inorg. Chim. Acta 2011, 369:253-259.
224. Yi C.S., Lee D.W. Organometallics 2009, 28:947-949.
225. Horning E.C., Horning M.G. J. Am. Chem. Soc. 1947, 69:1359-1361.
226. Newman M.S., Blum J. J. Am. Chem. Soc. 1964, 503-507.
227. Karakhanov R.A., Vartanyan M.M., Apandiev R.B., Karzhavina N.P. Izv. Akad. Nauk SSSR Ser. Khim. 1982, 1905.
228. Jones T.H., Fales H.M. Tetrahedron Lett. 1983, 24:5439-5440.
229. Williams E.A., Meikle R.W., Redemann C.T. J. Agric. Food. Chem. 1965, 13:210-213.
230. Hales N.J., Heaney H., Hollinshead J.H., Ley S.V. Tetrahedron 1995, 51:7741-7754.
231. Kamiguchi S., Nagashima S., Chihara T. Chem. Lett. 2007, 36:1340-1341.
232. Dong S., Qin T., Hamel E., Beutler J.A., Porco J.A. J. Am. Chem. Soc. 2012, 134:19782-19787.
233. Hayashi M., Shibuya M., Iwabuchi Y. Org. Lett. 2011, 14:154-157.
234. Vaz A.D.N., Chakraborty S., Massey V. Biochemistry 1995, 34:4246-4256.
235. Murthy Y.V.S.N., Meah Y., Massey V. J. Am. Chem. Soc. 1999, 121:5344-5345.
236. Schittmayer M., Glieder A., Uhl M.K., et al. Adv. Synth. Catal. 2011, 353:268-274.