Abstract
This review deals with organic reactions which are promoted by indium metal or indium salts, with a focus on recent advances in stoichiometric and catalytic pathways. Applications to transmetalations, cross-coupling reactions and carboindation, in which an organoindium species may be postulated, are highlighted, as well as the reactions in which a radical is the key intermediate. Special attention is placed on the role of indium metal as a reducer, and on the Lewis acidity of indium salts in catalytic processes.
1 Introduction
2 The Oxidation States of Indium
3 Barbier-Type Additions
4 Carbonyl Alkynylation
5 Carbonyl Additions via Transmetalation
6 Carboindation of Alkynes
7 Cross-Coupling Reactions
8 Nucleophilic Substitutions
9 Radical Reactions
10 Hydroindation
11 Reduction of Functional Groups
12 Activation of Silicon by Indium(III) Salts
13 Indium(III)-Catalyzed Reactions
14 Conclusion
Key words
indium metal - indium salts - reduction - metalation - Lewis acid
References
1
Araki S.
Ito H.
Butsugan Y.
J. Org. Chem.
1988,
53:
1831
2
Li C.-J.
Chan TH.
Tetrahedron Lett.
1991,
32:
7017
3
Li C.-J.
Chem. Rev.
1993,
93:
2023
4
Li C.-J.
Tetrahedron
1996,
52:
5643
5
Lubineau A.
Augé J.
Queneau Y.
Synthesis
1994,
741
6
Paquette LA. In
Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes
Anastas PT.
Williamson TC.
Oxford University Press;
Oxford:
1998.
p.250
7
Lubineau A.
Augé J.
Top. Curr. Chem.
1999,
206:
1
8
Ranu BC.
Eur. J. Org. Chem.
2000,
2347
9
Chauhan KK.
Frost CG.
J. Chem. Soc., Perkin Trans. 1
2000,
3015
10
Podlech J.
Maier TC.
Synthesis
2003,
633
11
Nair V.
Ros S.
Jayan CN.
Pillai BS.
Tetrahedron
2004,
60:
1959
12
Chan TH.
Yang Y.
J. Am. Chem. Soc.
1999,
121:
3228
13
Miyabe H.
Naito T.
Org. Biomol. Chem.
2004,
2:
1267
14
Shibata I.
Kato H.
Ishida T.
Yasuda M.
Baba A.
Angew. Chem. Int. Ed.
2004,
43:
711
15
Takami K.
Mikami S.
Yorimitsu H.
Shinokubo H.
Oshima K.
J. Org. Chem.
2003,
68:
6627
16
Loh T.-P.
Chua G.-L.
Chem. Commun.
2006,
2739
17
Preite MD.
Pérez-Carvajal A.
Synlett
2006,
3337
18
Tuck DG.
Chem. Soc. Rev.
1993,
269
19
Pardoe JA.
Downs AJ.
Chem. Rev.
2007,
107:
2
20
Gyname MJS.
Waterworth LG.
Worrall IJ.
J. Organomet. Chem.
1972,
40:
C9
21
Araki S.
Ito H.
Katsumura N.
Butsugan Y.
J. Organomet. Chem.
1989,
369:
291
22
Tyrra W.
Wickleder MS.
J. Organomet. Chem.
2003,
677:
28
23
Peppe C.
Tuck DG.
Victoriano L.
J. Chem. Soc., Dalton Trans.
1982,
2165
24
Marshall JA.
Grant CM.
J. Org. Chem.
1999,
64:
8214
25
Huang J.-M.
Xu K.-C.
Loh T.-P.
Synthesis
2003,
755
26
Augé J.
Lubin-Germain N.
Thiaw-Woaye A.
Tetrahedron Lett.
1999,
40:
9245
27
Augé J.
Lubin-Germain N.
Marque S.
Seghrouchni L.
J. Organomet. Chem.
2003,
679:
79
28
Chung WJ.
Higashiya S.
Oba Y.
Welch JT.
Tetrahedron
2003,
59:
10031
29
Juan S.
Hua Z.-H.
Qi S.
Ji S.-J.
Loh T.-P.
Synlett
2004,
829
30
Harthong S.
Billard T.
Langlois B.
Synthesis
2005,
2253
31
Kumar S.
Kumar V.
Chimni SS.
Tetrahedron Lett.
2003,
44:
2101
32
Cravotto G.
Giovenzana GB.
Maspero A.
Pilati T.
Penoni A.
Palmisano G.
Tetrahedron Lett.
2006,
47:
6439
33
Levoirier E.
Canac Y.
Norsikian S.
Lubineau A.
Carbohydr. Res.
2004,
339:
2737
34
Min J.-H.
Jung S.-Y.
Wu B.
Oh JT.
Lah MS.
Koo S.
Org. Lett.
2006,
8:
1459
35
Loh T.-P.
Tan K.-T.
Hu Q.-Y.
Tetrahedron Lett.
2001,
42:
8705
36
Tan K.-T.
Chng S.-S.
Cheng H.-S.
Loh T.-P.
J. Am. Chem. Soc.
2003,
125:
2958
37
Lombardo M.
Morganti S.
Trombini C.
J. Org. Chem.
2003,
68:
997
38
Lombardo M.
Licciulli S.
Trombini C.
Tetrahedron Lett.
2003,
44:
9147
39
Lombardo M.
Pasi F.
Trombini C.
Eur. J. Org. Chem.
2006,
3061
40
Paquette L. A.
Synthesis
2003,
765
41
Kim JH.
Seo WD.
Lee JH.
Lee BW.
Park KH.
Synthesis
2003,
2473
42
Chng S.-S.
Hoang T.-G.
Lee W.-WW.
Tham M.-P.
Ling HY.
Loh T.-P.
Tetrahedron Lett.
2004,
45:
9501
43
Loh T.-P.
Yin Z.
Song H.-Y.
Tan K.-L.
Tetrahedron Lett.
2003,
44:
911
44
Hirayama LC.
Gamsey S.
Knueppel D.
Steiner D.
DeLaTorre K.
Singaram B.
Tetrahedron Lett.
2005,
46:
2315
45
Lloyd-Jones GC.
Wall PD.
Slaughter JL.
Parker AJ.
Laffan DP.
Tetrahedron
2006,
62:
11402
46
Miao W.
Chung LW.
Wu Y.-D.
Chan TH.
J. Am. Chem. Soc.
2004,
126:
13326
47
Loh T.-P.
Lin M.-J.
Tan K.-L.
Tetrahedron Lett.
2003,
44:
507
48
Lin M.-J.
Loh T.-P.
J. Am. Chem. Soc.
2003,
125:
13042
49
Lu WL.
Ma J.
Yang Y.
Chan TH.
Org. Lett.
2000,
2:
3469
50
Miao W.
Lu W.
Chan TH.
J. Am. Chem. Soc.
2003,
125:
2412
51
Arimitsu S.
Hammond GB.
J. Org. Chem.
2006,
71:
8865
52
Arimitsu S.
Jacobsen JM.
Hammond GB.
Tetrahedron Lett.
2007,
48:
1625
53
Peppe C.
das Chagas RP.
Synlett
2006,
605
54
Babu SA.
Yasuda M.
Shibata I.
Baba A.
Org. Lett.
2004,
4475
55
Babu SA.
Yasuda M.
Shibata I.
Baba A.
J. Org. Chem.
2005,
70:
10408
56
Kumar S.
Kaur P.
Tetrahedron Lett.
2004,
45:
3413
57
Vilaivan T.
Winotapan C.
Banphavichit V.
Shinada T.
Ohfune Y.
J. Org. Chem.
2005,
70:
3464
58
Chen Q.
Qiu X.-L.
Qing F.-L.
J. Org. Chem.
2006,
71:
3762
59
Law MC.
Cheung TW.
Wong K.-Y.
Chan TH.
J. Org. Chem.
2007,
72:
923
60
Jang T.-S.
Ku W.
Jang MS.
Keum G.
Kang SB.
Chung BY.
Kim Y.
Org. Lett.
2006,
8:
195
61
Hirashita T.
Toumatsu S.
Imagawa Y.
Araki S.
Setsune J.
Tetrahedron Lett.
2006,
47:
1613
62
Bernardi L.
Cerè V.
Femoni C.
Pollicino S.
Ricci A.
J. Org. Chem.
2003,
68:
3348
63
Ritson DJ.
Cox RJ.
Berge J.
Org. Biomol. Chem.
2004,
2:
1921
64
Cook GR.
Maity BC.
Kargbo R.
Org. Lett.
2004,
6:
1741
65
Cook GR.
Kargbo R.
Maity B.
Org. Lett.
2005,
7:
2767
66
Foubelo F.
Yus M.
Tetrahedron: Asymmetry
2004,
15:
3823
67
Ranu B.
Das A.
Tetrahedron Lett.
2004,
45:
6875
68
Augé J.
Lubin-Germain N.
Seghrouchni L.
Tetrahedron Lett.
2002,
43:
5255
69
Augé J.
Lubin-Germain N.
Seghrouchni L.
Tetrahedron Lett.
2003,
44:
819
70
Picard J.
Lubin-Germain N.
Uziel J.
Augé J.
Synthesis
2006,
979
71
Sakai N.
Hirasawa M.
Konakahara T.
Tetrahedron Lett.
2003,
44:
4171
72
Takita R.
Fukuta Y.
Ohshima T.
Shibasaki M.
Org. Lett.
2005,
7:
1363
73
Takita R.
Yakura K.
Ohshima T.
Shibasaki M.
J. Am. Chem. Soc.
2005,
127:
13760
74
Marshall JA.
Hinkle KW.
J. Org. Chem.
1995,
60:
1920
75
Teo Y.-C.
Tan K.-T.
Loh T.-P.
Chem. Commun.
2005,
1318
76
Teo Y.-C.
Goh J.-D.
Loh T.-P.
Org. Lett.
2005,
2743
77
Teo Y.-C.
Goh E.-L.
Loh T.-P.
Tetrahedron Lett.
2005,
46:
6209
78
Lu J.
Hong M.-L.
Ji S.-J.
Loh T.-P.
Chem. Commun.
2005,
1010
79
Lu J.
Hong M.-L.
Ji S.-J.
Teo Y.-C.
Loh T.-P.
Chem. Commun.
2005,
4217
80
Lu J.
Ji S.-J.
Teo Y.-C.
Loh T.-P.
Org. Lett.
2005,
159
81
Teo Y.-C.
Goh E.-L.
Loh T.-P.
Tetrahedron Lett.
2005,
46:
4573
82
Lu J.
Ji S.-J.
Loh T.-P.
Chem. Commun.
2005,
2345
83
Lu J.
Ji S.-J.
Teo Y.-C.
Loh T.-P.
Tetrahedron Lett.
2005,
46:
7435
84
Yanada R.
Obika S.
Kono H.
Takemoto Y.
Angew. Chem. Int. Ed.
2006,
45:
3822
85
Yadav JS.
Reddy BVS.
Reddy MS.
Parimala G.
Synthesis
2003,
2390
86
Araki S.
Kamei T.
Hirashita T.
Yamamura H.
Kawai M.
Org. Lett.
2000,
2:
847
87
Hirashita T.
Kambe S.
Tsuji H.
Omori H.
Araki S.
J. Org. Chem.
2004,
69:
5054
88
Jang T.-S.
Keum G.
Kang SB.
Chung BY.
Kim Y.
Synthesis
2003,
775
89
Miyabe H.
Yamaoka Y.
Naito T.
Takemoto Y.
J. Org. Chem.
2003,
68:
6745
90
Marshall JA.
Palovich MR.
J. Org. Chem.
1997,
62:
6001
91
Marshall JA.
Eidam P.
Eidam HS.
J. Org. Chem.
2006,
71:
4840
92
Marshall JA.
Ellis KC.
Org. Lett.
2003,
5:
1729
93
Miyabe H.
Yamaoka Y.
Naito T.
Takemoto Y.
J. Org. Chem.
2004,
69:
1415
94
Yasuda M.
Miyai T.
Shibata I.
Baba A.
Nomura R.
Matsuda H.
Tetrahedron Lett.
1995,
36:
9497
95
Klaps E.
Schmid W.
J. Org. Chem.
1999,
64:
7537
96
Miao W.
Chan TH.
Synthesis
2003,
785
97
Lee PH.
Kim S.
Lee K.
Seomoon D.
Kim H.
Lee S.
Kim M.
Han M.
Noh K.
Livinghouse T.
Org. Lett.
2004,
6:
4825
98
Goeta A.
Salter MM.
Shah H.
Tetrahedron
2006,
62:
3582
99
Miura K.
Fujisawa N.
Hosomi A.
J. Org. Chem.
2004,
69:
2427
100
Miura K.
Fujisawa N.
Toyohara S.
Hosomi A.
Synlett
2006,
1883
101
Pérez I.
Sestelo JP.
Sarandeses LA.
Org. Lett.
1999,
1:
1267
102
Pérez I.
Sestelo JP.
Sarandeses LA.
J. Am. Chem. Soc.
2001,
123:
4155
103
Pena MA.
Sestelo JP.
Sarandeses LA.
Synthesis
2003,
780
104
Pena MA.
Sestelo JP.
Sarandeses LA.
Synthesis
2005,
485
105
Lehmann U.
Awasthi S.
Minehan T.
Org. Lett.
2003,
5:
2703
106
Qian M.
Huang Z.
Negishi E.
Org. Lett.
2004,
6:
1531
107
Hirashita T.
Hayashi Y.
Mitsui K.
Araki S.
J. Org. Chem.
2003,
68:
1309
108
Sakai N.
Annaka K.
Konakahara T.
Org. Lett.
2004,
6:
1527
109
Rodriguez D.
Sestelo JP.
Sarandeses LA.
J. Org. Chem.
2004,
69:
8136
110
Baker L.
Minehan T.
J. Org. Chem.
2004,
69:
3957
111
Metza JT.
Terzian RA.
Minehan T.
Tetrahedron Lett.
2006,
47:
8905
112
Riveiros R.
Rodriguez D.
Sestelo JP.
Sarandeses LA.
Org. Lett.
2006,
8:
1403
113
Black DA.
Arndtsen BA.
Org. Lett.
2006,
8:
1991
114
Oh BK.
Cha JH.
Cho YS.
Choi KI.
Koh HY.
Chang MH.
Pae AN.
Tetrahedron Lett.
2003,
44:
2911
115
Hirashita T.
Mitsui K.
Hayashi Y.
Araki S.
Tetrahedron Lett.
2004,
45:
9189
116
Lee K.
Kim H.
Miura T.
Kiyota K.
Kusama H.
Kim S.
Iwasawa N.
Lee PH.
J. Am. Chem. Soc.
2003,
125:
9682
117
Rodriguez D.
Sestelo JP.
Sarandeses LA.
J. Org. Chem.
2003,
68:
2518
118
Cho YS.
Jun BY.
Pae AN.
Cha JH.
Koh HY.
Chang MH.
Han S.-Y.
Synthesis
2004,
2620
119
Ferrier RJ.
Zubkov OA.
Org. React. (N.Y.)
2003,
62:
569
120
Price S.
Edwards S.
Wu T.
Minehan T.
Tetrahedron Lett.
2004,
45:
5197
121 Augé, J.; Lubin-Germain, N.; Uziel, J. unpublished results.
122
Takami K.
Usugi S.
Yorimitsu H.
Oshima K.
Synthesis
2005,
824
123
Yanada R.
Koh Y.
Nishimori N.
Matsumura A.
Obika S.
Mitsuya H.
Fujii N.
Takemoto Y.
J. Org. Chem.
2004,
69:
2417
124
Yanada R.
Obika S.
Nishimori N.
Yamauchi M.
Takemoto Y.
Tetrahedron Lett.
2004,
45:
2331
125
Yanada R.
Obika S.
Oyama M.
Takemoto Y.
Org. Lett.
2004,
6:
2825
126
Hirashita T.
Tanaka J.
Hayashi A.
Araki S.
Tetrahedron Lett.
2005,
46:
289
127
Keh CCK.
Wie C.
Li C.-J.
J. Am. Chem. Soc.
2003,
125:
4062
128
Ranu B.
Mandal T.
Tetrahedron Lett.
2006,
47:
2859
129
Miyabe H.
Ueda M.
Nishimura A.
Naito T.
Tetrahedron
2004,
60:
4227
130
Sugi M.
Sakuma D.
Togo H.
J. Org. Chem.
2003,
68:
7629
131
Miyai T.
Inoue K.
Yasuda M.
Baba A.
Tetrahedron Lett.
1998,
39:
1929
132
Hayashi N.
Honda H.
Yasuda M.
Shibata I.
Baba A.
Org. Lett.
2006,
8:
4553
133
Inoue K.
Sawada A.
Shibata I.
Baba A.
J. Am. Chem. Soc.
2002,
124:
906
134
Ranu BC.
Das A.
Hajra A.
Synthesis
2003,
1012
135
Ranu BC.
Banerjee S.
Das A.
Tetrahedron Lett.
2004,
45:
8579
136
Das B.
Banerjee J.
Chowdhury N.
Majhi A.
Holla H.
Synlett
2006,
1879
137
Ranu BC.
Samanta S.
Tetrahedron
2003,
59:
7901
138
Ranu BC.
Samanta S.
J. Org. Chem.
2003,
68:
7130
139
Wang C.
Pan Y.
Yang D.
J. Organomet. Chem.
2005,
690:
1705
140
Wang C.
Yan I.
Zheng Z.
Yang D.
Pan Y.
Tetrahedron
2006,
62:
7712
141
Xue Z.
Yang DY.
Wang CY.
J. Organomet. Chem.
2006,
691:
247
142
Wang C.-Y.
Su H.
Yang D.-Y.
Synlett
2004,
561
143
Qin Y.-Y.
Yang Y.-Y.
Qiu X.-L.
Qing F.-L.
Synthesis
2006,
1475
144
Takami K.
Yorimitsu H.
Oshima K.
Org. Lett.
2004,
6:
4555
145
Takami K.
Mikami S.
Yorimitsu H.
Shinokubo H.
Oshima K.
Tetrahedron
2003,
59:
6627
146
Hayashi N.
Shibata I.
Baba A.
Org. Lett.
2004,
6:
4981
147
Benati L.
Bencivenni G.
Leardini R.
Nanni D.
Minozzi M.
Spagnolo P.
Scialpi R.
Zanardi G.
Org. Lett.
2006,
8:
2499
148
Miura K.
Yamada Y.
Tomita M.
Hosomi A.
Synlett
2004,
1985
149
Miura K.
Tomita M.
Yamada Y.
Hosomi A.
J. Org. Chem.
2007,
72:
787
150
Hayashi N.
Shibata I.
Baba A.
Org. Lett.
2005,
7:
3093
151
Pitts MR.
Harrison JR.
Moody CJ.
J. Chem. Soc., Perkin Trans. 1
2001,
955
152
Bernardi L.
Bonini BF.
Capito E.
Dessole G.
Comes-Franchini M.
Fochi M.
Ricci A.
J. Org. Chem.
2004,
69:
8168
153
Cicchi S.
Bonanni M.
Cardona F.
Revuelta J.
Goti A.
Org. Lett.
2003,
5:
1773
154
Kim BH.
Han R.
Piao F.
Jun YM.
Baik W.
Lee BM.
Tetrahedron Lett.
2003,
44:
77
155
Chen L.
Li Z.
Li C.-H.
Synlett
2003,
732
156
Han R.
Son KI.
Ahn GH.
Jun YM.
Lee BM.
Park Y.
Kim BH.
Tetrahedron Lett.
2006,
47:
7295
157
Mahesh M.
Murphy JA.
Wessel HP.
J. Org. Chem.
2005,
70:
4118
158
Wang C.
Pan Y.
Wu A.
Tetrahedron
2007,
63:
429
159
Ranu BC.
Mandal T.
Synlett
2004,
1239
160
Ranu BC.
Mandal T.
Tetrahedron Lett.
2006,
47:
6911
161
Ranu BC.
Mandal T.
Can. J. Chem.
2006,
84:
762
162
Ranu BC.
Mandal T.
J. Org. Chem.
2004,
69:
5793
163
Ranu BC.
Chattopadhyay K.
Banerjee S.
J. Org. Chem.
2006,
71:
423
164
Ranu BC.
Mandal T.
Samanta S.
Org. Lett.
2003,
5:
1439
165
Peppe C.
Lang ES.
Ledesma GN.
de Castro LB.
do Rego Barros OS.
de Azevedo Mello P.
Synlett
2005,
3091
166
Tiwari P.
Misra AK.
Tetrahedron Lett.
2006,
47:
2345
167
Munbunjong W.
Lee EH.
Chavasiri W.
Jang DO.
Tetrahedron Lett.
2005,
46:
8769
168
Ranu BC.
Mandal T.
Tetrahedron Lett.
2006,
47:
5677
169
Ranu BC.
Das A.
Adv. Synth. Catal.
2005,
347:
712
170
Cho S.
Kang S.
Keum G.
Kang SB.
Han S.-Y.
Kim Y.
J. Org. Chem.
2003,
68:
180
171
Mukaiyama T.
Ohno T.
Nishimura T.
Han JS.
Kobayashi S.
Chem. Lett.
1990,
2239
172
Yang L.
Xu L.-W.
Xia C.-G.
Tetrahedron Lett.
2007,
48:
1599
173
Onishi Y.
Ito T.
Yasuda M.
Baba A.
Tetrahedron
2002,
58:
8227
174
Onishi Y.
Ogawa D.
Yasuda M.
Baba A.
J. Am. Chem. Soc.
2002,
124:
13691
175
Yasuda M.
Yamasaki S.
Onishi Y.
Baba A.
J. Am. Chem. Soc.
2004,
126:
7186
176
Babu SA.
Yasuda M.
Baba A.
Org. Lett.
2007,
9:
405
177
Yasuda M.
Onishi Y.
Ueba M.
Miyai T.
Baba A.
J. Org. Chem.
2001,
66:
7741
178
Yasuda M.
Saito T.
Ueba M.
Baba A.
Angew. Chem. Int. Ed.
2004,
43:
1414
179
Saito T.
Yasuda M.
Baba A.
Synlett
2005,
1737
180
Saito T.
Nishimoto Y.
Yasuda M.
Baba A.
J. Org. Chem.
2006,
71:
8516
181
Wabnitz TC.
Yu J.-Q.
Spencer JB.
Chem. Eur. J.
2004,
10:
484
182
Fu F.
Teo Y.-C.
Loh T.-P.
Org. Lett.
2006,
8:
5999
183
Harada S.
Handa S.
Matsunaga S.
Shibasaki M.
Angew. Chem. Int. Ed.
2005,
44:
4365
184
Gregg BT.
Earley WG.
Golden KC.
Quinn JF.
Razzano DA.
Rennells WM.
Synthesis
2006,
4200
185
Munoz-Muniz O.
Quintanar-Audelo M.
Juaristi E.
J. Org. Chem.
2003,
68:
1622
186
Fu F.
Teo Y.-C.
Loh T.-P.
Tetrahedron Lett.
2006,
47:
4267
187
Loh T.-P.
Chen S.-L.
Org. Lett.
2002,
4:
3647
188
Chen S.-L.
Ji S.-J.
Loh T.-P.
Tetrahedron Lett.
2003,
44:
2405
189
Anniyappan M.
Muralidharan D.
Perumal PT.
Vittal JJ.
Tetrahedron
2004,
60:
2965
190
Friestad GK.
Korapala CS.
Ding H.
J. Org. Chem.
2006,
71:
281
191
Ranu BC.
Hajra A.
Jana U.
J. Org. Chem.
2000,
65:
6270
192
Martins MAP.
Teixeira MVM.
Cunico W.
Scapin E.
Mayer R.
Pereira CMP.
Zanatta N.
Bonacorso HG.
Peppe C.
Yuan Y.-F.
Tetrahedron Lett.
2004,
45:
8991
193
Yadav JS.
Reddy BVS.
Venugopal C.
Padmavani B.
Tetrahedron Lett.
2004,
45:
7507
194
Nakamura M.
Endo K.
Nakamura E.
J. Am. Chem. Soc.
2003,
125:
13002
195
Nakamura M.
Endo K.
Nakamura E.
Org. Lett.
2005,
7:
3279
196
Yasuda M.
Somyo T.
Baba A.
Angew. Chem. Int. Ed.
2006,
45:
793
197
Zhang Y.
Li C.-J.
Angew. Chem. Int. Ed.
2006,
45:
1949
198
Zhang Y.
Li C.-J.
J. Am. Chem. Soc.
2006,
128:
4242
199
Yang J.
Viswanathan GS.
Li C.-J.
Tetrahedron Lett.
1999,
40:
1627
200
Yang X.-F.
Mague JT.
Li C.-J.
J. Org. Chem.
2001,
66:
739
201
Chan K.-P.
Loh T.-P.
Tetrahedron Lett.
2004,
45:
8387
202
Chan K.-P.
Loh T.-P.
Org. Lett.
2005,
7:
4491
203
Chan K.-P.
Seow A.-H.
Loh T.-P.
Tetrahedron Lett.
2007,
48:
37
204
Lee C.-HA.
Loh T.-P.
Tetrahedron Lett.
2006,
47:
1641
205
Loh T.-P.
Tan K.-T.
Hu Q.-Y.
Angew. Chem. Int. Ed.
2001,
40:
2921
206
Dobbs AP.
Martinovic S.
Tetrahedron Lett.
2002,
43:
7055
207
Dobbs AP.
Guesné SJJ.
Martinovic S.
Coles SJ.
Hursthouse MB.
J. Org. Chem.
2003,
68:
7880
208
Yadav JS.
Reddy BVS.
Bhaishya G.
Green Chem.
2003,
5:
264
209
Lee C.-HA.
Loh T.-P.
Tetrahedron Lett.
2004,
45:
5819
210
Loh T.-P.
Hu Q.-Y.
Chok Y.-K.
Tan K.-T.
Tetrahedron Lett.
2001,
42:
9277
211
Loh T.-P.
Lee C.-LK.
Tan K.-T.
Org. Lett.
2002,
4:
2985
212
Lee K.-C.
Lin M.-J.
Loh T.-P.
Chem. Commun.
2004,
2456
213
Loh T.-P.
Hu Q.-Y.
Tan K.-T.
Cheng H.-S.
Org. Lett.
2001,
3:
2669
214
Chen S.-L.
Hu Q.-Y.
Loh T.-P.
Org. Lett.
2004,
6:
3365
215
Loh T.-P.
Feng L.-C.
Yang J.-Y.
Synthesis
2002,
937
216
Cheng H.-S.
Loh T.-P.
J. Am. Chem. Soc.
2003,
125:
4990
217
Ranu BC.
Jana R.
Samanta S.
Adv. Synth. Catal.
2004,
346:
446
218
Smith BM.
Graham AE.
Tetrahedron Lett.
2006,
47:
9317
219
Ceschi MA.
de Arunja Felix L.
Peppe C.
Tetrahedron Lett.
2000,
41:
9695
220
Muthusamy S.
Babu SA.
Gunanathan C.
Tetrahedron
2002,
58:
7897
221
Yin L.
Zhang Z.-H.
Wang Y.-M.
Pang M.-L.
Synlett
2004,
1727
222
Zhang Z.-H.
Yin L.
Li Y.
Wang Y.-M.
Tetrahedron Lett.
2005,
46:
889
223
Das SK.
Reddy KA.
Krovvidi VLNR.
Mukkanti K.
Carbohydr. Res.
2005,
340:
1387
224
Chauban KK.
Frost CG.
Love I.
Waite D.
Synlett
1999,
1743
225
Yadav JS.
Reddy BVS.
Basak AK.
Baishya G.
Narsaiah V.
Synthesis
2006,
3831
226
Chankeshwara SV.
Chakraborti AK.
Synthesis
2006,
2784
227
Jang DO.
Moon KS.
Cho DH.
Kim J.-G.
Tetrahedron Lett.
2006,
47:
6063
228
Ding R.
Zhang HB.
Chen YJ.
Liu L.
Wang D.
Li CJ.
Synlett
2004,
555
229
Yadav JS.
Reddy BVS.
Rao KV.
Rao PP.
Raj KS.
Prasad AR.
Prabhakar A.
Jagadeesh B.
Synlett
2006,
3447
230
Nagarajan R.
Perumal PT.
Tetrahedron
2002,
58:
1229
231
Yadav JS.
Reddy BVS.
Krishna AD.
Swamy T.
Tetrahedron Lett.
2003,
44:
6055
232
Sun H.-B.
Hua R.
Yin Y.
Tetrahedron Lett.
2006,
47:
2291
233
Tsuchimoto T.
Hatanaka K.
Shirakawa E.
Kawakami Y.
Chem. Commun.
2003,
2454
234
Tsuchimoto T.
Matsubayashi H.
Kaneko M.
Shirakawa E.
Kawakami Y.
Angew. Chem. Int. Ed.
2005,
44:
1336
235
Weïner M.
Dunach E.
Tetrahedron Lett.
2006,
47:
287
236
Weïner M.
Coulombel L.
Dunach E.
Chem. Commun.
2006,
332
237
Peppe C.
Lang ES.
Molinos de Andrade F.
Borges de Castro L.
Synlett
2004,
1723
238
Morikawa S.
Yamazaki S.
Furusaki Y.
Amano N.
Zenke K.
Kakiuchi K.
J. Org. Chem.
2006,
71:
3540
239
Sakai N.
Annaka K.
Konakahara T.
Tetrahedron Lett.
2006,
47:
631
240
Sakai N.
Annaka K.
Konakahara T.
J. Org. Chem.
2006,
71:
3653
241
Miyanohana Y.
Chatani N.
Org. Lett.
2006,
8:
2155
242
Yadav JS.
Reddy BVS.
Baishya G.
Synlett
2003,
396
243
Kim SH.
Shin C.
Pae AN.
Koh HY.
Chang MH.
Chung BY.
Cho YS.
Synthesis
2004,
1581
244
Yoo KH.
Choi EB.
Lee HK.
Yeon GH.
Yang HC.
Pak CS.
Synthesis
2006,
1599
245
Cook GR.
Hayashi R.
Org. Lett.
2006,
8:
1045
246
Babu BS.
Balasubramanian KK.
Tetrahedron Lett.
2000,
41:
1271
247
Das SK.
Reddy KA.
Roy J.
Synlett
2003,
1607
248
Ghosh R.
Chakraborty A.
Maiti DK.
Puranik VG.
Tetrahedron Lett.
2005,
46:
8047
249
Yadav JS.
Reddy BVS.
Synthesis
2002,
511
250
Yadav JS.
Reddy BVS.
Raju AK.
Rao CV.
Tetrahedron Lett.
2002,
43:
5437
251
Das SK.
Reddy KA.
Abbineni C.
Roy J.
Rao KVLN.
Sachwani RH.
Iqbal J.
Tetrahedron Lett.
2003,
44:
4507
252
Yadav JS.
Raju AK.
Sunitha V.
Tetrahedron Lett.
2006,
47:
5269
253
Yadav JS.
Reddy BVS.
Rao KV.
Raj KS.
Prasad AR.
Kumar SK.
Kunwar AC.
Jayaprakash P.
Jagannath B.
Angew. Chem. Int. Ed.
2003,
42:
5198
254
Mukherjee D.
Sarkar SK.
Chowdhury US.
Taneja SC.
Tetrahedron Lett.
2007,
48:
663
255
Mukherjee D.
Ray PK.
Chowdhury US.
Tetrahedron
2001,
57:
7701
256
Das SK.
Roy J.
Reddy KA.
Abbineni C.
Carbohydr. Res.
2003,
338:
2237
257
Kobayashi S.
Nagaayama S.
Busujima T.
J. Am. Chem. Soc.
1998,
120:
8287
258
Yang J.-Z.
Tian P.
Xu W.-G.
Liu S.-Z.
Thermochim. Acta
2004,
412:
1
259
Da Silveira Neto BA.
Ebeling G.
Gonçalves RS.
Gozzo FC.
Eberlin MN.
Dupont J.
Synthesis
2004,
1155