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1
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8444252168
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For a recent review of the catalytic asymmetric nitroaldol reaction, see: Palomo, C.; Oiarbide, M.; Mielgo, A. Angew. Chem., Int. Ed. 2004, 43, 5442.
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(c) Lu, S. F.; Du, D. M.; Zhang, S. W.; Xu, J. Tetrahedron: Asymmetry 2004, 15, 3433.
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Lu, S.F.1
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(d) Du, D.-M.; Lu, S.-F.; Fang, T.; Xu, J. J.Org. Chem. 2005, 70, 3712.
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(e) Choudary, B. M.; Ranganath, K. V. S.; Pal, U.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2005, 127, 13167.
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(f) Li, H.; Wang, B.; Deng, L. J. Am. Chem. Soc. 2006, 128, 732.
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Li, H.1
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8
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0036146812
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One example using 2,2,2-trifluoroacetophenone to give the product with low ee (21% ee) was reported. Misumi, Y.; Bulman, R. A.; Matsumoto, K. Heterocycles 2002, 56, 599.
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Heterocycles
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Misumi, Y.1
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84980189236
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(a) Seebach, D.; Lehr, F. Angew. Chem., Int. Ed. Engl. 1976, 15, 505.
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Seebach, D.1
Lehr, F.2
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12
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0030788440
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-
For asymmetric nitroaldol reaction of aldehydes using LLB 2a, see review: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236. For other examples of catalytic asymmetric nitroaldol reactions of aldehydes, see ref 1.
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Shibasaki, M.1
Sasai, H.2
Arai, T.3
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13
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-
33748516010
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-
note
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-1.
-
-
-
-
16
-
-
33748515077
-
-
note
-
(R)-LLB 2a also promoted nitroaldol reactions of other simple ketones in high enantioselectivity, albeit in poor yields. Ketone 3d (90% ee, 5% yield); 3e (89% ee, 20% yield).
-
-
-
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17
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0033581160
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-
and references therein
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For an elegant kinetic resolution of tertiary aldols via retro-aldol reaction with a catalytic antibody, see: (a) List, B.; Shabat, D.; Zhong, G.; Turner, J. M.; Li, A.; Bui, T.; Anderson, J.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 1999, 121, 7283 and references therein.
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List, B.1
Shabat, D.2
Zhong, G.3
Turner, J.M.4
Li, A.5
Bui, T.6
Anderson, J.7
Lerner, R.A.8
Barbas III, C.F.9
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18
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0030056177
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For a retronitroaldol reaction with a catalytic antibody, see: (b) Flanagan, M. E.; Jacobsen, J. R.; Sweet, E.; Schultz, P. G. J. Am. Chem. Soc. 1996, 118, 6078.
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Flanagan, M.E.1
Jacobsen, J.R.2
Sweet, E.3
Schultz, P.G.4
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19
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21344465658
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Recent general review for nonenzymatic kinetic resolution: (a) Vedejs, E.; Jure, M. Angew. Chem., Int. Ed. 2005, 44, 3974.
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Vedejs, E.1
Jure, M.2
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20
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33646121294
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-
and references therein
-
For examples of nonenzymatic kinetic resolution of tert-alcohols, see: (b) Angione, M. C.; Miller, S. J. Tetrahedron 2006, 62, 5254 and references therein.
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(2006)
Tetrahedron
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Angione, M.C.1
Miller, S.J.2
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21
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-
33748510031
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-
note
-
The absolute configurations of 4a, 4e, and 4f were determined to be R after conversion into known compounds. See Supporting Information.
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-
-
-
22
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-
0002178750
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-
The s values in this paper were calculated based on conversion and ee of recovered 4 assuming first-order kinetic dependence on 4. Kinetic studies are required to determine accurate s values. For discussion on the validity of calculated s values, see: Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5. See also ref 9a.
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Adv. Synth. Catal.
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Keith, J.M.1
Larrow, J.F.2
Jacobsen, E.N.3
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23
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3042835317
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Reviews: (a) Ding, K.; Du, H.; Yuan, Y.; Long, J. Chem.-Eur. J. 2004, 10, 2872.
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Chem.-Eur. J.
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Ding, K.1
Du, H.2
Yuan, Y.3
Long, J.4
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25
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0037045239
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For selected examples, see: (c) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10.
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Long, J.1
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26
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0037450022
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(d) Reetz, M. T.; Shell, T.; Meiswinkel, A.; Mehler, G. Angew. Chem., Int. Ed. 2003, 42, 790.
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Reetz, M.T.1
Shell, T.2
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27
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0041495679
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(e) Peña, D.; Minnaard, A. J.; Boogers, J. A. F.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. Org. Biomol. Chem. 2003, 1, 1087.
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Peña, D.1
Minnaard, A.J.2
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De Vries, A.H.M.4
De Vries, J.G.5
Feringa, B.L.6
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28
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-
1942436903
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-
and references therein
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2: Meyers, A. I.; Nelson, T. D.; Moorlag, H.; Rawson, D. J.; Meier, A. Tetrahedron 2004. 60, 4459 and references therein.
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Meyers, A.I.1
Nelson, T.D.2
Moorlag, H.3
Rawson, D.J.4
Meier, A.5
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29
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33748492405
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note
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Because the known synthetic methods of racemic tertiary nitroaldols did not afford satisfactory yield for 4f, we developed a new synthetic method. See Supporting Information for details.
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-
-
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30
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4744353743
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Ligand liability of related rare earth-alkali metal heterobimetallic complexes was reported. (a) Bari, L. D.; Lelli, M.; Salvadori, P. Chem.-Eur. J. 2004, 10, 4594.
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Bari, L.D.1
Lelli, M.2
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31
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24644494677
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See also: (b) Horiuchi, Y.; Gnanadesikan, V.; Ohshima, T.; Masu, H.; Katagiri, K.; Sei, Y.; Yamaguchi, K.; Shibasaki, M. Chem-Eur. J. 2005, 11, 5195.
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Horiuchi, Y.1
Gnanadesikan, V.2
Ohshima, T.3
Masu, H.4
Katagiri, K.5
Sei, Y.6
Yamaguchi, K.7
Shibasaki, M.8
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32
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33748510253
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note
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For full details of ESI-MS data [m/z 200-1300] of LLB 2a, LLB* 2b, 2a/2b = 2:1. and 2a/2b = 1:2, see Supporting Information. Although it is impossible to discuss quantitatively using MS, we believe the ESI-MS data at least suggested the presence of mixed-ligand La-Li complexes in the mixture of LLB 2a and LLB* 2b. NMR analysis only resulted in a complex mixture spectrum.
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33
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0000083032
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Matt, C.; Wagner, A.; Mioskowski, C. J. Org. Chem. 1997, 62, 234.
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Matt, C.1
Wagner, A.2
Mioskowski, C.3
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