-
1
-
-
33750507943
-
-
For recent reports of catalyzed C-C, C-N, and C-O bond formation through direct substitution of allylic or propargylic alcohols with nucleophiles, see: a
-
For recent reports of catalyzed C-C, C-N, and C-O bond formation through direct substitution of allylic or propargylic alcohols with nucleophiles, see: a) V. Terrasson, S. Marque, J.-M. Campagne, D. Prim, Adv. Synth. Catal. 2006, 348, 2063;
-
(2006)
Adv. Synth. Catal
, vol.348
, pp. 2063
-
-
Terrasson, V.1
Marque, S.2
Campagne, J.-M.3
Prim, D.4
-
2
-
-
33746709483
-
-
b) Z. Zhan, W. Wang, R. Yang, J. Yu, J. Li, H. Liu, Chem. Commun. 2006, 3352;
-
(2006)
Chem. Commun
, pp. 3352
-
-
Zhan, Z.1
Wang, W.2
Yang, R.3
Yu, J.4
Li, J.5
Liu, H.6
-
3
-
-
33846439597
-
-
c) Y. Nishibayashi, A. Shinoda, Y. Miyake, H. Matsuzawa, M. Sato, Angew. Chem. 2006, 118, 4953;
-
(2006)
Angew. Chem
, vol.118
, pp. 4953
-
-
Nishibayashi, Y.1
Shinoda, A.2
Miyake, Y.3
Matsuzawa, H.4
Sato, M.5
-
5
-
-
33846434303
-
-
d) K. Motokura, N. Fujita, K. Mori, T. Mizugaki, K. Ebitani, K. Kaneda, Angew. Chem. 2006, 118, 2667;
-
(2006)
Angew. Chem
, vol.118
, pp. 2667
-
-
Motokura, K.1
Fujita, N.2
Mori, K.3
Mizugaki, T.4
Ebitani, K.5
Kaneda, K.6
-
7
-
-
34250870917
-
-
e) H. Qin, N. Yamagiwa, S. Matsunaga, M. Shibasaki, Angew. Chem. 2007, 119, 413;
-
(2007)
Angew. Chem
, vol.119
, pp. 413
-
-
Qin, H.1
Yamagiwa, N.2
Matsunaga, S.3
Shibasaki, M.4
-
9
-
-
33749315860
-
-
f) R. Sanz, A. Martínez, D. Miguel, J. M. Álvarez- Guitiérrez, F. Rodríguez, Adv. Synth. Catal. 2006, 348, 1841;
-
(2006)
Adv. Synth. Catal
, vol.348
, pp. 1841
-
-
Sanz, R.1
Martínez, A.2
Miguel, D.3
Álvarez- Guitiérrez, J.M.4
Rodríguez, F.5
-
10
-
-
33750432179
-
-
g) T. Saito, Y. Nishimoto, M. Yasuda and A. Baba, J. Org. Chem. 2006, 71, 8516;
-
(2006)
J. Org. Chem
, vol.71
, pp. 8516
-
-
Saito, T.1
Nishimoto, Y.2
Yasuda, M.3
Baba, A.4
-
11
-
-
33749370349
-
-
h) M. Yasuda, T. Somyo, A. Baba, Angew. Chem. 2006, 118, 807;
-
(2006)
Angew. Chem
, vol.118
, pp. 807
-
-
Yasuda, M.1
Somyo, T.2
Baba, A.3
-
13
-
-
34249288620
-
-
i) R. Sanz, D. Miguel, A. Martinez, J. M. Alvarez-Gutiérrez, F. Rodrìguez, Org. Lett. 2007, 9, 2027;
-
(2007)
Org. Lett
, vol.9
, pp. 2027
-
-
Sanz, R.1
Miguel, D.2
Martinez, A.3
Alvarez-Gutiérrez, J.M.4
Rodrìguez, F.5
-
14
-
-
33947182489
-
-
j) M. Rueping, B. J. Nachtsheim, A. Kuenkel, Org. Lett. 2007, 9, 825;
-
(2007)
Org. Lett
, vol.9
, pp. 825
-
-
Rueping, M.1
Nachtsheim, B.J.2
Kuenkel, A.3
-
15
-
-
34447324093
-
-
k) M. Noji, Y. Konno, Keitaro Ishii, J. Org. Chem. 2007, 72, 5161.
-
(2007)
J. Org. Chem
, vol.72
, pp. 5161
-
-
Noji, M.1
Konno, Y.2
Ishii, K.3
-
16
-
-
60149086735
-
-
For valuable transformations on water or in the presence of water, see: a a C.-J. Li, T.-H. Chan, Organic Reaction in Aqueous Media, Wiley, New York, 1997;
-
For valuable transformations "on water" or "in the presence of water", see: a a) C.-J. Li, T.-H. Chan, Organic Reaction in Aqueous Media, Wiley, New York, 1997;
-
-
-
-
17
-
-
60149103075
-
-
Organic Synthesis in Water (Ed.: P. A. Grieco), Blackie Academic and Professional, London, 1998;
-
b) Organic Synthesis in Water (Ed.: P. A. Grieco), Blackie Academic and Professional, London, 1998;
-
-
-
-
18
-
-
24044470646
-
-
c) C.-J. Li, Chem. Rev. 2005, 105, 3095;
-
(2005)
Chem. Rev
, vol.105
, pp. 3095
-
-
Li, C.-J.1
-
20
-
-
60149102858
-
-
Organic Reaction in Water (Ed.: U. M. Lindström), Blackwell Publishing, Oxford, 2007;
-
e)Organic Reaction in Water (Ed.: U. M. Lindström), Blackwell Publishing, Oxford, 2007;
-
-
-
-
23
-
-
34547145881
-
-
g) D. G. Blackmond, A. Armstrong, V. Coombe, A, Wells, Angew. Chem. 2007, 119, 3872;
-
(2007)
Angew. Chem
, vol.119
, pp. 3872
-
-
Blackmond, D.G.1
Armstrong, A.2
Coombe, V.3
Wells, A.4
-
25
-
-
20544435104
-
-
h) S. Narayan, J. Muldoon, M. G. Finn, V. V. Fokin, H. C. Kolb, K. B. Sharpless, Angew. Chem. 2005, 117, 3219;.
-
(2005)
Angew. Chem
, vol.117
, pp. 3219
-
-
Narayan, S.1
Muldoon, J.2
Finn, M.G.3
Fokin, V.V.4
Kolb, H.C.5
Sharpless, K.B.6
-
26
-
-
60149087986
-
-
Chem. Int. Ed. 2005, 44, 3157.
-
(2005)
Chem. Int. Ed
, vol.44
, pp. 3157
-
-
-
32
-
-
0037241494
-
-
H. Mayr, B. Kempf, A. R. Ofial, Acc. Chem. Res. 2003, 36, 66.
-
(2003)
Acc. Chem. Res
, vol.36
, pp. 66
-
-
Mayr, H.1
Kempf, B.2
Ofial, A.R.3
-
33
-
-
0038509986
-
-
B. Kempf, N. Hampel, A. R. Ofial, H. Mayr, Chem. Eur. J. 2003, 9, 2209.
-
(2003)
Chem. Eur. J
, vol.9
, pp. 2209
-
-
Kempf, B.1
Hampel, N.2
Ofial, A.R.3
Mayr, H.4
-
34
-
-
38349100690
-
-
a) S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471;
-
(2007)
Chem. Rev
, vol.107
, pp. 5471
-
-
Mukherjee, S.1
Yang, J.W.2
Hoffmann, S.3
List, B.4
-
35
-
-
0034654216
-
-
b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395;
-
(2000)
J. Am. Chem. Soc
, vol.122
, pp. 2395
-
-
List, B.1
Lerner, R.A.2
Barbas III, C.F.3
-
49
-
-
55249111616
-
-
k) P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. 2008, 120, 6232;
-
(2008)
Angew. Chem
, vol.120
, pp. 6232
-
-
Melchiorre, P.1
Marigo, M.2
Carlone, A.3
Bartoli, G.4
-
56
-
-
0345825852
-
-
For the first nucleophilic substitution proceeding under enamine catalysis, see: a
-
For the first nucleophilic substitution proceeding under enamine catalysis, see: a) N. Vignola, B. List, J. Am. Chem. Soc. 2004, 126, 450;
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 450
-
-
Vignola, N.1
List, B.2
-
57
-
-
31144440036
-
-
b) A. Fu, B. List, W. Thiel, J. Org. Chem. 2006, 71, 320.
-
(2006)
J. Org. Chem
, vol.71
, pp. 320
-
-
Fu, A.1
List, B.2
Thiel, W.3
-
58
-
-
34848814187
-
-
For organocatalytic domino reactions consisting of a Michael addition and subsequent intramolecular a alkylation, see: c H. Xie, L. Zu, H. Li, J. Wang, W. Wang, J. Am. Chem. Soc. 2007, 129, 10886;
-
For organocatalytic domino reactions consisting of a Michael addition and subsequent intramolecular a alkylation, see: c) H. Xie, L. Zu, H. Li, J. Wang, W. Wang, J. Am. Chem. Soc. 2007, 129, 10886;
-
-
-
-
59
-
-
34447533890
-
-
d) R. Rios, H. Sunden, J. Vesely, G.-L. Zhao, P. Dziedzic, A. Còrdova, Adv. Synth. Catal. 2007, 349, 1028;
-
(2007)
Adv. Synth. Catal
, vol.349
, pp. 1028
-
-
Rios, R.1
Sunden, H.2
Vesely, J.3
Zhao, G.-L.4
Dziedzic, P.5
Còrdova, A.6
-
60
-
-
34447511093
-
-
e) R. Rios, J. Vesely, H. Sunden, I. Ibrahem, G.-L. Zhao, A. Còrdova, Tetrahedron Lett. 2007, 48, 5835;
-
(2007)
Tetrahedron Lett
, vol.48
, pp. 5835
-
-
Rios, R.1
Vesely, J.2
Sunden, H.3
Ibrahem, I.4
Zhao, G.-L.5
Còrdova, A.6
-
63
-
-
53349122064
-
-
Recently, MacMillan reported an interesting methodology for highly enantioselective alkylation of aldehydes by photochemical activation of α-carbonyl compounds, see
-
Recently, MacMillan reported an interesting methodology for highly enantioselective alkylation of aldehydes by photochemical activation of α-carbonyl compounds, see: D. A. Nice-wicz, D. W. C. MacMillan, Science 2008, 322, 77.
-
(2008)
Science
, vol.322
, pp. 77
-
-
Nice-wicz, D.A.1
MacMillan, D.W.C.2
-
64
-
-
85200105936
-
-
The SOMO activation, developed by MacMillan and co-workers, is also another important strategy for the α-alkylation of aldehydes: T. D. Beeson, A. Mastracchio, J. Hong, K. Ashton, D. W. C. MacMillan, Science 2007, 316, 582.
-
The SOMO activation, developed by MacMillan and co-workers, is also another important strategy for the α-alkylation of aldehydes: T. D. Beeson, A. Mastracchio, J. Hong, K. Ashton, D. W. C. MacMillan, Science 2007, 316, 582.
-
-
-
-
65
-
-
55049118534
-
-
D. Enders, A. A. Narine, F. Toulgoat, T. Bisschops, Angew. Chem. 2008, 120, 5744;
-
(2008)
Angew. Chem
, vol.120
, pp. 5744
-
-
Enders, D.1
Narine, A.A.2
Toulgoat, F.3
Bisschops, T.4
-
67
-
-
60149089206
-
-
R. R. Shaikh, A. Mazzanti, M. Petrini, G. Bartoli, P. Melchiorre, Angew. Chem. 2008, 120, 8835;
-
(2008)
Angew. Chem
, vol.120
, pp. 8835
-
-
Shaikh, R.R.1
Mazzanti, A.2
Petrini, M.3
Bartoli, G.4
Melchiorre, P.5
-
69
-
-
33845183755
-
-
The 4,4′-bis(dimethylamino)diphenylmethane carbocation has a half-life of 10-20 seconds; see: R. A. McCLelland, V. M. Kana-gasabapathy, N. S. Banait, S. J. Steenken, J. Am. Chem. Soc. 1989, 111, 3966.
-
The 4,4′-bis(dimethylamino)diphenylmethane carbocation has a half-life of 10-20 seconds; see: R. A. McCLelland, V. M. Kana-gasabapathy, N. S. Banait, S. J. Steenken, J. Am. Chem. Soc. 1989, 111, 3966.
-
-
-
-
70
-
-
33745715054
-
-
and references therein. For theoretical investigations, see
-
G. Lelais, D. W. C. MacMillan, Aldrichimica Acta 2006, 39, 79, and references therein. For theoretical investigations, see:
-
(2006)
Aldrichimica Acta
, vol.39
, pp. 79
-
-
Lelais, G.1
MacMillan, D.W.C.2
-
71
-
-
59649089543
-
-
a) J. B. Brazier, G. Evans, T. J. K. Gibbs, S. J. Coles, M. B. Hursthouse, J. A. Platts, N. C. O. Tomkinson, Org. Lett. 2009, 11, 133;
-
(2009)
Org. Lett
, vol.11
, pp. 133
-
-
Brazier, J.B.1
Evans, G.2
Gibbs, T.J.K.3
Coles, S.J.4
Hursthouse, M.B.5
Platts, J.A.6
Tomkinson, N.C.O.7
-
73
-
-
60149092084
-
-
The major diastereoisomer and the absolute configuration obtained in the reaction using ferrocenyl alcohol 4 were assigned on the basis of: a The reaction of alcohol (S)-4 with racemic G occurrs with retention of configuration;
-
The major diastereoisomer and the absolute configuration obtained in the reaction using ferrocenyl alcohol 4 were assigned on the basis of: a) The reaction of alcohol (S)-4 with racemic G occurrs with retention of configuration;
-
-
-
-
74
-
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60149090650
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-
The major diastereo-isomer obtained with racemic or optically active alcohol 4 is the same;
-
b) The major diastereo-isomer obtained with racemic or optically active alcohol 4 is the same;
-
-
-
-
75
-
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60149103573
-
-
The optically active catalyst G affords products having an S configuration at C2. For the proposed model, see the Supporting Information.
-
c) The optically active catalyst G affords products having an S configuration at C2. For the proposed model, see the Supporting Information.
-
-
-
-
76
-
-
52949138243
-
-
G. Valero, A.-N. Balaguer, A. Moyano, R. Rios, Tetrahedron Lett. 2008, 49, 6559.
-
(2008)
Tetrahedron Lett
, vol.49
, pp. 6559
-
-
Valero, G.1
Balaguer, A.-N.2
Moyano, A.3
Rios, R.4
-
77
-
-
38349147664
-
-
For reactions in which 3-(1arylsulfonylalkyl)indoles are used as suitable electrophilic precursors, see
-
a) For reactions in which 3-(1arylsulfonylalkyl)indoles are used as suitable electrophilic precursors, see: R. Ballini, A. Palmieri, M. Petrini, R. R. Shaikh, Adv. Synth. Catal. 2008, 350, 129;
-
(2008)
Adv. Synth. Catal
, vol.350
, pp. 129
-
-
Ballini, R.1
Palmieri, A.2
Petrini, M.3
Shaikh, R.R.4
-
79
-
-
33748948395
-
-
c) R. Ballini, A. Palmieri, M. Petrini, E. Torregiani, Org. Lett. 2006, 8, 4093.
-
(2006)
Org. Lett
, vol.8
, pp. 4093
-
-
Ballini, R.1
Palmieri, A.2
Petrini, M.3
Torregiani, E.4
-
82
-
-
60149103074
-
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Alcohol 5 provided little control in the diastereoselection, which is probably caused by the fast reaction of the carbocation formed under the reaction conditions. The simple stereoselection of our reaction was different from what was obtained by Petrini and Melchiorre et al.: see reference [12].
-
Alcohol 5 provided little control in the diastereoselection, which is probably caused by the fast reaction of the carbocation formed under the reaction conditions. The simple stereoselection of our reaction was different from what was obtained by Petrini and Melchiorre et al.: see reference [12].
-
-
-
-
83
-
-
60149092841
-
-
S. Lakhdar, T. Tokuyasu, H. Mayr, Angew. Chem. 2008, 120, 8851;
-
(2008)
Angew. Chem
, vol.120
, pp. 8851
-
-
Lakhdar, S.1
Tokuyasu, T.2
Mayr, H.3
-
85
-
-
33746590748
-
-
For diastereoselective nucleophilic additions, see: a
-
For diastereoselective nucleophilic additions, see: a) F. Mühlthau, D. Stadler, A. Goeppert, G. A. Olah, G. K. S. Prakash, T. Bach, J. Am. Chem. Soc. 2006, 128, 9668;
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 9668
-
-
Mühlthau, F.1
Stadler, D.2
Goeppert, A.3
Olah, G.A.4
Prakash, G.K.S.5
Bach, T.6
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