-
1
-
-
38349178582
-
-
(a) Erkkila, A.; Majander, I.; Pihko, P. M. Chem. Rev. 2007, 107, 5416.
-
(2007)
Chem. Rev
, vol.107
, pp. 5416
-
-
Erkkila, A.1
Majander, I.2
Pihko, P.M.3
-
2
-
-
38349100690
-
-
(b) Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. 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
-
3
-
-
0033714636
-
-
(c) Fache, F.; Schulz, E.; Tommasino, M. L.; Lemaire, M. Chem. Rev. 2000, 100, 2159.
-
(2000)
Chem. Rev
, vol.100
, pp. 2159
-
-
Fache, F.1
Schulz, E.2
Tommasino, M.L.3
Lemaire, M.4
-
4
-
-
33845282886
-
-
(a) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551.
-
(1987)
J. Am. Chem. Soc
, vol.109
, pp. 5551
-
-
Corey, E.J.1
Bakshi, R.K.2
Shibata, S.3
-
5
-
-
0032541271
-
-
(b) Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986.
-
(1986)
Angew. Chem., Int. Ed
, vol.1998
, pp. 37
-
-
Corey, E.J.1
Helal, C.J.2
-
6
-
-
38949133131
-
-
(a) Zhu, S.; Yu, S.; Ma, D. Angew. Chem., Int. Ed. 2008, 47, 545.
-
(2008)
Angew. Chem., Int. Ed
, vol.47
, pp. 545
-
-
Zhu, S.1
Yu, S.2
Ma, D.3
-
8
-
-
53349159499
-
-
(c) Hayashi, Y.; Itoh, T.; Aratake, S.; Ishikawa, H. Angew. Chem., Int. Ed. 2008, 47, 2082.
-
(2008)
Angew. Chem., Int. Ed
, vol.47
, pp. 2082
-
-
Hayashi, Y.1
Itoh, T.2
Aratake, S.3
Ishikawa, H.4
-
9
-
-
43549118736
-
-
(d) Chu, Q.; Yu, M. S.; Curran, D. P. Org. Lett. 2008, 10, 749.
-
(2008)
Org. Lett
, vol.10
, pp. 749
-
-
Chu, Q.1
Yu, M.S.2
Curran, D.P.3
-
11
-
-
34547178180
-
-
(f) Aleman, J.; Cabrera, S.; Maerten, E.; Overgaard, J.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 5520.
-
(2007)
Angew. Chem., Int. Ed
, vol.46
, pp. 5520
-
-
Aleman, J.1
Cabrera, S.2
Maerten, E.3
Overgaard, J.4
Jorgensen, K.A.5
-
13
-
-
33845505476
-
-
(h) Palomo, C.; Mielgo, A. Angew. Chem., Int. Ed. 2006, 45, 7876.
-
(2006)
Angew. Chem., Int. Ed
, vol.45
, pp. 7876
-
-
Palomo, C.1
Mielgo, A.2
-
14
-
-
0346267223
-
-
Mathre, D. J.; Jones, T. K.; Xavier, L. C.; Blacklock, T. J.; Reamer, R. A.; Mohan, J. J.; Jones, E. T. T.; Hoogsteen, K.; Baum, M. W.; Grabowski, E. J. J. J. Org. Chem. 1991, 56, 751.
-
(1991)
J. Org. Chem
, vol.56
, pp. 751
-
-
Mathre, D.J.1
Jones, T.K.2
Xavier, L.C.3
Blacklock, T.J.4
Reamer, R.A.5
Mohan, J.J.6
Jones, E.T.T.7
Hoogsteen, K.8
Baum, M.W.9
Grabowski, E.J.J.10
-
15
-
-
0000920450
-
-
Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231.
-
(1994)
J. Am. Chem. Soc
, vol.116
, pp. 3231
-
-
Beak, P.1
Kerrick, S.T.2
Wu, S.3
Chu, J.4
-
16
-
-
0000311992
-
-
For other examples of synthesis of α,α-disubstituted 2-pyrrolidinylmethanols from reaction of 2-lithiopyrrolidines with symmetrical ketones or aldehydes, see also: (a) Reitz, D. B.; Beak, P.; Tse, A. J. Org. Chem. 1981, 46, 4316.
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For other examples of synthesis of α,α-disubstituted 2-pyrrolidinylmethanols from reaction of 2-lithiopyrrolidines with symmetrical ketones or aldehydes, see also: (a) Reitz, D. B.; Beak, P.; Tse, A. J. Org. Chem. 1981, 46, 4316.
-
-
-
-
19
-
-
33747761620
-
-
(d) Coldham, I.; Dufour, S.; Haxell, T. F. N.; Patel, J. J.; Sanchez-Jimenez, G. J. Am. Chem. Soc. 2006, 128, 10943.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 10943
-
-
Coldham, I.1
Dufour, S.2
Haxell, T.F.N.3
Patel, J.J.4
Sanchez-Jimenez, G.5
-
20
-
-
36749046756
-
-
Kagan, H.; Namy, J. L.; Girard, P. Tetrahedron Suppl. 1981, 37, 175.
-
(1981)
Tetrahedron Suppl
, vol.37
, pp. 175
-
-
Kagan, H.1
Namy, J.L.2
Girard, P.3
-
21
-
-
3543057490
-
-
For reviews, see: a
-
For reviews, see: (a) Edmonds, D. J.; Johnston, D.; Procter, D. J. Chem. Rev. 2004, 104, 3371.
-
(2004)
Chem. Rev
, vol.104
, pp. 3371
-
-
Edmonds, D.J.1
Johnston, D.2
Procter, D.J.3
-
25
-
-
0036263466
-
-
Masson, G.; Py, S.; Vallee, Y. Angew. Chem., Int. Ed. 2002, 41, 1772.
-
(2002)
Angew. Chem., Int. Ed
, vol.41
, pp. 1772
-
-
Masson, G.1
Py, S.2
Vallee, Y.3
-
26
-
-
22144488443
-
-
(a) Goti, A.; Cardona, F.; Soldaini, G. Org. Synth. 2005, 81, 204.
-
(2005)
Org. Synth
, vol.81
, pp. 204
-
-
Goti, A.1
Cardona, F.2
Soldaini, G.3
-
28
-
-
0000465072
-
-
(c) Murray, R. W.; Iyanar, K.; Chen, J.; Wearing, J. T. J. Org. Chem. 1996, 61, 8099.
-
(1996)
J. Org. Chem
, vol.61
, pp. 8099
-
-
Murray, R.W.1
Iyanar, K.2
Chen, J.3
Wearing, J.T.4
-
30
-
-
33845282438
-
-
Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C.-P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925.
-
(1987)
J. Am. Chem. Soc
, vol.109
, pp. 7925
-
-
Corey, E.J.1
Bakshi, R.K.2
Shibata, S.3
Chen, C.-P.4
Singh, V.K.5
-
32
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59949091325
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General Procedure for the Synthesis of α,α-Disubstituted 2-Pyrrolidinylmethanols 2-7. Method A (for aromatic ketones, To a stirred and carefully deoxygenated solution of the nitrone 1 (60 mg, 0.7 mmol) and aromatic ketone (0.5 mmol) in dry THF was added a 0.1 M solution of SmI2 (11.0 mL, 1.1 mmol) at -78°C under argon. After 15 min, degassed water (36 μL, 2.0 mmol) and SmI2 (14.0 mL, 1.4 mmol) were added, and the reaction mixture was allowed to reach room temperature. After 1 h, a saturated solution of Na2S2O3 (5 mL) and 1 M NaOH solution (15 mL) were added, and the mixture was extracted with EtOAc (20 mL, Usual workup yielded racemic products 2-5. Method B (for aliphatic ketones, Same procedure as for method A, but degassed water (90 μL, 5.0 mmol) was added at the beginning of the reaction products 6 and 7
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3 (5 mL) and 1 M NaOH solution (15 mL) were added, and the mixture was extracted with EtOAc (20 mL). Usual workup yielded racemic products 2-5. Method B (for aliphatic ketones): Same procedure as for method A, but degassed water (90 μL, 5.0 mmol) was added at the beginning of the reaction (products 6 and 7).
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0029584795
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Reiners, I.; Wilken, J.; Martens, J. Tetrahedron: Asymmetry 1995, 6, 3063.
-
(1995)
Tetrahedron: Asymmetry
, vol.6
, pp. 3063
-
-
Reiners, I.1
Wilken, J.2
Martens, J.3
-
34
-
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0035356735
-
-
and references therein
-
Periasamy, M.; Kumar, N. S.; Sivakumar, S.; Rao, V. D.; Ramanathan, C. R.; Venkatraman, L. J. Org. Chem. 2001, 66, 3828, and references therein.
-
(2001)
J. Org. Chem
, vol.66
, pp. 3828
-
-
Periasamy, M.1
Kumar, N.S.2
Sivakumar, S.3
Rao, V.D.4
Ramanathan, C.R.5
Venkatraman, L.6
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35
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59949095587
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2 reaction mixture; see the Supporting Information.
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2 reaction mixture; see the Supporting Information.
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36
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0020246368
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Seebach, D.; Prelog, V. Angew. Chem., Int. Ed. 1982, 21, 654.
-
(1982)
Angew. Chem., Int. Ed
, vol.21
, pp. 654
-
-
Seebach, D.1
Prelog, V.2
-
37
-
-
19544379547
-
-
See for examples: a
-
See for examples: (a) Aspinall, H. C.; Greeves, N.; Valla, C. Org. Lett. 2005, 7, 1919.
-
(2005)
Org. Lett
, vol.7
, pp. 1919
-
-
Aspinall, H.C.1
Greeves, N.2
Valla, C.3
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39
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59949097022
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See the Supporting Information
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See the Supporting Information.
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40
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59949083856
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Determined by chiral HPLC on a Daicel Chiralpak AD-RH column, acetonitrile/water; see the Supporting Information
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Determined by chiral HPLC on a Daicel Chiralpak AD-RH column, acetonitrile/water; see the Supporting Information.
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