Enantioselective radical reactions

Topics in Current Chemistry

Volumn 263, Issue , 2006, Pages 107-162

  Zimmerman, Jake ^a   Sibi, Mukund P ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

Atom transfer; Chiral Lewis acid; Conjugate addition; Electron transfer; Enantioselective radical reactions

Indexed keywords

EID: 33748870454     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/128_027     Document Type: Review

References (167)

1. Renaud P, Sibi MP (eds) (2001) Radicals in Organic Synthesis, vols 1 and 2. Wiley, Weinheim
2. Parsons AF (2000) An Introduction to Free Radical Chemistry. Blackwell Science, Oxford
3. Alfassi ZB (1999) General Aspects of the Chemistry of Radicals. Wiley, New York
4. Fossey J, Lefort D, Sorba J (1995) Free Radical in Organic Chemistry. Wiley, New York
5. Giese B (1986) Radicals in Organic Synthesis. Formation of Carbon-Carbon Bonds. Pergamon, Oxford
6. Curran DP (1991) Radical Addition Reactions. In: Trost BM, Fleming I, Semmelheck MF (eds) Comprehensive Organic Synthesis. Pergamon, Oxford, p 715-777
7. Curran DP, Porter NA, Giese B (1995) Stereochemistry of Radical Reactions. Wiley, Weinheim
8. Smadja W (1994) Synlett 1-26
9. Beckwith AL (1993) Chem Soc Rev 22:143-151
10. Porter NA, Giese B, Curran DP (1991) Acc Chem Res 24:296-301
11. Giese B (1989) Angew Chem Int Ed Engl 28:969-980
12. Sibi MP, Manyem S, Zimmerman J (2003) Chem Rev 103:3263-3295
13. Sibi MP, Rheault TR (2001) In: Renaud P, Sibi MP (eds) Radicals in Organic Synthesis. Wiley, Weinheim, p 461-478
14. Parsons AF, Bar G (2003) Chem Soc Rev 251-263
15. Sibi MP, Porter NA (1999) Acc Chem Res 32:163-171
16. Gawley RE, Aube J (1996) Principles of Asymmetric Synthesis. Pergamon, Oxford, p 14
17. Perlmutter P (1992) Conjugate Addition Reactions in Organic Synthesis. Pergamon Press, Oxford
18. Sibi MP, Manyem S (2000) Tetrahedron 56:8033-8061
19. Jasperse CP, Curran DP, Fevig TL (1991) Chem Rev 91:1237-1286
20. Curran DP (2000) Aldrichimica Acta 33:104-110
21. Murakata M, Tsutsui H, Takeuchi N, Hoshino O (1999) Tetrahedron 55:10295-10304
22. Urabe H, Yamashita K, Suzuki K, Kobayashi K, Sato P (1995) J Org Chem 60:3576-3577
23. Sibi MP, Sausker JB (2002) J Am Chem Soc 124:984-991
24. Sugimoto H, Nakamura S, Watanabe Y, Toru T (2003) Tetrahedron: Asymmetry 14:3043-3055
25. Sibi MP, Asano Y, Sausker JB (2001) Angew Chem Int Ed 40:1293-1296
26. Liu M, Sibi MP (2002) Tetrahedron 58:7991-8035
27. Juaristi E, Lopez-Ruiz H (1999) Curr Med Chem 6:983-1004
28. Davies HML, Venkataramani C (2002) Angew Chem Int Ed 41:2197-2199
29. Duursma A, Minnaard AJ, Feringa BL (2003) J Am Chem Soc 125:3700-3701
30. Sibi MP, Patil K (2004) Angew Chem Int Ed 43:1235-1238
31. Basavaiah D, Rao AJ, Satyanarayana T (2003) Chem Rev 103:811-891
32. Langer P (2003) Org Synth Highlights V, p 165-177
33. Langer P (2000) Angew Chem Int Ed 39:3049-3052
34. Ciganek E (1997) Organic Reactions. New York 51:201-350
35. Basavaiah D, Rao PD, Hyma RS (1996) Tetrahedron 52:8001-8062
36. Sibi MP, Zimmerman J, Rheault T (2003) Angew Chem Int Ed 43:4521-4523
37. Garner P, Anderson JT, Cox PB, Klippenstein SJ, Leslie R, Scardovi N (2002) J Org Chem 67:6195-6209
38. Lee E, Tae JS, Lee C, Park CM (1993) Tetrahedron Lett 34:4831-4834
39. Sibi MP, Patil K (2005) Org Lett 7:1453-1456
40. Aechtner T, Dressel M, Bach T (2004) Angew Chem Int Ed 43:5849-5851
41. Buckmelter AJ, Kim AI, Rychnovsky SD (2000) J Am Chem Soc 122:9386-9390
42. Dalgard JE, Rychnovsky SD (2004) Org Lett 6:2713-2716
43. Ohno A, Ikeguchi M, Kimura T, Oka S (1979) J Am Chem Soc 101:7036-7040
44. Tanner DD, Kharrat A (1988) J Am Chem Soc 110:2968-2970
45. Gielen M, Mokhtar-Jamai H (1975) Bull Chem Soc Belg 84:197-202
46. Gielen M, Tondeur Y (1979) J Organomet Chem 169:265-281
47. Schumann H, Pachaly B, Schütze BC (1984) J Organomet Chem 169:145-152
48. Nanni D, Curran DP (1996) Tetrahedron: Asymmetry 7:2417-2422
49. Blumenstein M, Schwarzkopf K, Metzger JO (1997) Angew Chem Int Ed Engl 36:235-236
50. Blumenstein M, Lemmler M, Hayen A, Metzger JO (2003) Tetrahedron: Asymmetry 14:3069-3077
51. Schwarzkopf K, Blumenstein M, Hayen A, Metzger JO (1998) Eur J Org Chem, p 177-181
52. Helliwell M, Thomas EJ, Townsend LA (2002) J Chem Soc Perkin Trans 1:1286-1296
53. Dakternieks D, Dunn K, Perchyonok VT, Schiesser CH (1999) Chem Commun, p 1665-1666
54. Dakternieks D, Perchyonok VT, Schiesser CH (2003) Tetrahedron: Asymmetry 14:3057-3068
55. Dakternieks D, Dunn K, Henry DJ, Schiesser CH, Tiekink ERT (1999) Organomet 18:3342-3347
56. Dakternieks D, Dunn K, Schiesser CH, Tiekink ERT (2000) J Organomet Chem 605:209-220
57. Zeng L, Perchyonok VT, Schiesser CH (2004) Tetrahedron: Asymmetry 15:995-999
58. Dakternieks D, Schiesser CH (2001) Aust J Chem 54:89-91
59. Schiesser CH, Skidmore MA, White JM (2001) Aust J Chem 54:199-204
60. Kang J, Kim TH (2003) Bull Korean Chem Soc 24:1055-1056
61. Zeng L, Dakternieks D, Duthie A, Perchyonok VT, Schiesser CH (2004) Tetrahedron: Asymmetry 15:2547-2554
62. Curran DP, Gualtieri G (2001) Synlett 1038-1041
63. Gualtieri G, Geib SJ, Curran DP (2003) J Org Chem 68:5013-5019
64. Mok PLH, Roberts BP (1992) Tetrahedron Lett 33:7249-7252
65. Mok PLH, Roberts BP, McKetty PT (1993) J Chem Soc Perkin Trans 2:665-674
66. Dang H-S, Diart V, Roberts BP (1994) J Chem Soc Perkin Trans 1:1033-1041
67. Dang H-S, Diart V, Roberts BP, Tocher DA (1994) J Chem Soc Perkin Trans 2:1039-1045
68. Haque MB, Roberts BP (1996) Tetrahedron Lett 37:9123-9126
69. Haque MB, Roberts BP, Tocher DA (1998) J Chem Soc Perkin Trans 1:2881-2889
70. Cai Y, Roberts BP, Tocher DA (2002) J Chem Soc Perkin Trans 1:1376-1386
71. Dang H-S, Roberts BP (1995) Tetrahedron Lett 36:3731-3734
72. Dang H-S, Kim K-M, Roberts BP (1998) Chem Commun 1413-1414
73. Byers J (2001) In: Renaud P, Sibi MP (eds) Radicals in Organic Synthesis, vol 1. Wiley, Weinheim, p 72-89
74. Kameyama M, Kamigata N (1989) Bull Chem Soc Jpn 62:648-650
75. Kameyama M, Kamigata N, Kobayashi M (1987) J Org Chem 52:3312-3316
76. Kameyama M, Kamigata N (1987) Bull Chem Soc Jpn 60:3687-3691
77. Murai S, Sugise R, Sonoda N (1981) Angew Chem Int Ed Engl 20:475-476
78. Mero CL, Porter NA (1999) J Am Chem Soc 121:5155-5160
79. Brunner H, Bluchel C, Doyle MP (1997) J Organomet Chem 541:89-95
80. Yang D, Gu S, Yan YL, Zhu NY, Cheung KK (2001) J Am Chem Soc 123:8612-8613
81. Yang D, Gu S, Yan YL, Zhao HW, Zhu NY (2002) Angew Chem Int Ed 41:3014-3017
82. Miyabe H, Ushiro C, Ueda M, Yamakawa K, Naito T (2000) J Org Chem 65:176-185
83. Halland N, Jørgensen KA (2001) J Chem Soc Perkin Trans 1:1290-1295
84. Friestad GK, Shen Y, Ruggles EL (2003) Angew Chem Int Ed 42:5061-5063
85. Sibi MP, Manyem S (2000) Tetrahedron 56:8033-8061
86. Sibi MP, Ji JG, Wu JH, Gürtler S, Porter NA (1996) J Am Chem Soc 118:9200-9201
87. Sibi MP, Ji JG (1997) J Org Chem 62:3800-3801
88. Sibi MP, Petrovic G (2003) Tetrahedron: Asymmetry 14:2879-2882
89. Iserloh U, Curran DP, Kanemasa S (1999) Tetrahedron: Asymmetry 10:2417-2428
90. Murakata M, Tsutsui H, Hoshino O (2001) Org Lett 3:299-302
91. Sibi MP, Shay JJ, Ji JG (1997) Tetrahedron Lett 38:5955-5958
92. Sibi MP, Prabagaran N (2004) Synlett 2421-2424
93. Sibi MP, Manyem S (2002) Org Lett 4:2929-2932
94. Kobayashi S, Sugiura M, Kitagawa H, Lam WWL (2002) Chem Rev 102:2227-2302
95. Sibi MP, He L (2004) Org Lett 6:1749-1752
96. Sibi MP, Guerrero M (2005) Synthesis 1529-1532
97. Otera J (ed) (2000) Modern Carbonyl Chemistry. Wiley, Weinheim
98. Alcaide B, Almendros P (2002) Eur J Org Chem 65:1595-1601
99. Johnson JS, Evans DA (2000) Acc Chem Res 33:325-335
100. Trost BM, Ito H (2000) J Am Chem Soc 122:12003-12004
101. List B, Lerner RA, Barbas CF (2000) J Am Chem Soc 122:2395-2396
102. Singer RA, Carreira EM (1995) J Am Chem Soc 117:12360-12361
103. Garner P, Anderson JT, Cox PB, Klippenstein SJ, Leslie R, Scardovi N (2002) J Org Chem 67:6195-6209
104. Garner P, Anderson JT (1999) Org Lett 1:1057-1059
105. Guindon Y, Denis RC (1998) Tetrahedron Lett 39:339-342
106. Lee E, Tae JS, Lee C, Park CM (1993) Tetrahedron Lett 34:4831-4834
107. Lee E, Yoo S-K, Choo H, Song HY (1998) Tetrahedron Lett 39:317-318
108. Evans PA, Murthy VS, Roseman JD, Rheingold AL (1999) Angew Chem Int Ed 38:3175-3177
109. Lee E, Choi SJ (1999) Org Lett 1:1127-1128
110. Sibi MP, Liu M (2001) Curr Org Chem 5:719-755
111. Yamada K-I, Arai T, Sasai H, Shibasaki M (1998) J Org Chem 63:3666-3672
112. Arai T, Sasai H, Aoe K, Okamura K, Date T, Shibasaki M (1996) Angew Chem Int Ed Engl 35:104-106
113. Naasz R, Arnold LA, Pineschi M, Keller E, Feringa BL (1999) J Am Chem Soc 121:1104-1105
114. Alexakis A, Trevitt GP, Bernardinelli G (2001) J Am Chem Soc 123:4358-4359
115. Arnold LA, Naasz R, Minnaard AJ, Feringa BL (2001) J Am Chem Soc 123:5841-5842
116. Doi H, Sakai T, Iguchi M, Yamada K-I, Tomioka K (2003) J Am Chem Soc 125:2886-2887
117. Nishimura K, Tomioka K (2002) J Org Chem 67:431-434
118. Curran DP, Porter NA, Giese B (1995) Stereochemistry of Radical Reactions. Wiley, Weinheim
119. Durkin K, Liotta D, Rancourt J, Lavallée J-F, Boisvert L, Guindon Y (1992) J Am Chem Soc 114:4912-4914
120. Guindon Y, Houde K, Prevost M, Cardinal-David B, Landry SR, Daoust B, Bencheqroun M, Guerin B (2001) J Am Chem Soc 123:8496-8501
121. Curran DP, Abraham AC (1993) Tetrahedron 49:4821-4840
122. Curran DP, Ramamoorthy PS (1993) Tetrahedron 49:4841-4858
123. Curran DP, Geib S, De Mello N (1999) Tetrahedron 55:5681-5704
124. Kopping B, Chatgilialoglu C, Zehnder M, Giese B (1992) J Org Chem 57:3994-4000
125. Sibi MP, Petrovic G, Zimmerman J (2005) J Am Chem Soc 127:2390-2391
126. Evans DA, Tedrow JS, Shaw JT, Downey CW (2002) J Am Chem Soc 124:392-393
127. Denmark SE, Wynn T, Beutner GL (2002) J Am Chem Soc 124:13405-13407
128. Ghosh AK, Kim J-H (2003) Org Lett 5:1063-1066
129. Kiyooka S (2003) Tetrahedron: Asymmetry 14:2897-2910
130. Walker MA, Heathcock CH (1991) J Org Chem 56:5747-5750
131. Corey EJ, Kim SS (1990) J Am Chem Soc 112:4976-4977
132. Evans DA, Downey CW, Shaw JT, Tedrow JS (2002) Org Lett 4:1127-1130
133. He L, Srikanth GSC, Castle SL (2005) J Org Chem 70:8140-8147
134. Nishida M, Hayashi H, Nishida A, Kawahara N (1996) Chem Commun 579-580
135. Hiroi K, Ishii M (2000) Tetrahedron Lett 41:7071-7074
136. Curran DP, Liu W, Chen CH-T (1999) J Am Chem Soc 121:11012-11013
137. Petit M, Lapierre AJB, Curran DP (2005) J Am Chem Soc 127, ASAP
138. Rosenstein IJ (2001) In: Renaud P, Sibi MP (eds) Radicals in Organic Synthesis, vol 1. Wiley, Weinheim, p 50-71
139. Keck GE, Yates JB (1982) J Org Chem 47:3590-3591
140. Porter NA, Wu JHL, Zhang GR, Reed AD (1997) J Org Chem 62:6702-6703
141. Fhal AR, Renaud P (1997) Tetrahedron Lett 38:2661-2664
142. Porter NA, Feng H, Kavrakova IK (1999) Tetrahedron Lett 40:6713-6716
143. Murakata M, Jono T, Mizuno Y, Hoshino O (1997) J Am Chem Soc 119:11713-11714
144. Murakata M, Jono T, Hoshino O (1998) Tetrahedron: Asymmetry 9:2087-2092
145. Wu JH, Radinov R, Porter NA (1995) J Am Chem Soc 117:11029-11030
146. Wu JH, Zhang GR, Porter NA (1997) Tetrahedron Lett 38:2067-2070
147. Sibi MP, Ji JG (1996) J Am Chem Soc 118:3063
148. Watanabe Y, Mase N, Furue R, Toru T (2001) Tetrahedron Lett 42:2981-2984
149. Sibi MP, Chen J (2001) J Am Chem Soc 123:9472-9473
150. Sibi MP, Manyem S, Subramaniam R (2003) Tetrahedron 59:10575-10580
151. Gansäuer A, Bluhm H (2000) Chem Rev 100:2771-2788
152. Gansäuer A, Narayan S (2002) Adv Synth Catal 344:465-475
153. Kikukawa T, Hanamoto T, Inanaga J (1999) Tetrahedron Lett 40:7497-7500
154. Riber D, Hazell R, Skrydstrup T (2000) J Org Chem 65:5382-5390
155. Mikami K, Yamaoka M (1998) Tetrahedron Lett 39:4501-4504
156. Clerici A, Clerici L, Porta O (1996) Tetrahedron Lett 37:3035-3038
157. Matsubara S, Hashimoto Y, Okano T, Utimoto K (1999) Synlett 1411
158. Hashimoto Y, Mizuno U, Matsuoka H, Miyahara T, Takakura M, Yoshimoto M, Oshima K, Utimoto K, Matsubara S (2001) J Am Chem Soc 123:1503-1504
159. Enders D, Ullrich EC (2000) Tetrahedron: Asymmetry 11:3861-3865
160. Dunlap MS, Nicholas KM (1999) Synth Commun 27:1097-1106
161. Bandini M, Cozzi PG, Morganti S, Umani-Ronchi A (1999) Tetrahedron Lett 40:1997-2000
162. Bensari A, Renaud JL, Riant O (2001) Org Lett 3:3863-3865
163. Gansäuer A, Bluhm H, Lauterbach T (2001) Adv Synth Catal 343:785-787
164. Gansäuer A, Lauterbach T, Bluhm H, Noltemeyer M (1999) Angew Chem Int Ed 38:2909-2910
165. Kurihara M, Hayashi T, Miyata N (2001) Chem Lett 1324-1325
166. Nguyen PQ, Schäfer HJ (2001) Org Lett 3:2993-2995
167. Masutani K, Irie R, Katsuki T (2002) Chem Lett 36-37