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For a review on the stereoselective synthesis of γ-AAs, see
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For a review on the stereoselective synthesis of γ-AAs, see: Ordonez, M.; Cativiela, C. Tetrahedron: Asymmetry 2007, 18, 3-99.
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For a review on conjugate additions of nitrocompounds, see: Ballini, R.; Bosica, G.; Fiorini, D.; Palmieri, A.; Petrini, M. Chem. Rev. 2005, 105, 933-971.
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For reviews on asymmetric conjugate additions covering metal catalysis, see: (a) Covering organocatalysis
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For reviews on asymmetric conjugate additions covering metal catalysis, see: (a) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033-8061. Covering organocatalysis:
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Almasi, D.1
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Iminium ion mediated additions to enals: (a)
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Iminium ion mediated additions to enals: (a) Zu, L.; Xie, H.; Li, H.; Wang, J.; Wang, W. Adv. Synth. Catal. 2007, 349, 2660-2664.
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(c) Hojabri, L.; Hartikka, A.; Moghaddam, F. M.; Arvidsson, P. I. Adv. Synth. Catal. 2007, 349, 740-748.
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40149109031
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Bifunctional thiourea-catalyzed additions to unsaturated N-acyl pyrroles
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(d) Wang, Y.; Li, P.; Liang, X.; Zhang, T. Y.; Ye, J. Chem. Commun. 2008, 1232-1234. Bifunctional thiourea-catalyzed additions to unsaturated N-acyl pyrroles:
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Chem. Commun.
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Wang, Y.1
Li, P.2
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Ye, J.5
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14
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43449135616
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Diphenylprolinol-catalyzed cross-conjugate additions between nitroalkenes and enals
-
(e) Vakulya, B.; Varga, S.; Soós, T. J. Org. Chem. 2008, 13, 3475-3480. Diphenylprolinol-catalyzed cross-conjugate additions between nitroalkenes and enals:
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Vakulya, B.1
Varga, S.2
Soós, T.3
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Iminium ion mediated additions to enones
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(f) Zhong, C.; Chen, Y.; Petersen, J. L.; Akhmedov, N. G.; Shi, X. Angew. Chem., Int. Ed 2009, 48, 1279-1282. Iminium ion mediated additions to enones:
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Zhong, C.1
Chen, Y.2
Petersen, J.L.3
Akhmedov, N.G.4
Shi, X.5
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16
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64649093783
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For methods involving β-unsubstituted vinyl ketones that provide from poor to moderate ee, see the following. Al-catalyzed addition of nitroesters
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(g) Dong, L.-t.; Lu, R.-j.; Du, Q.-s.; Zhang, J.-m.; Liu, S.-p.; Xuan, Y.-n.; Yan, M. Tetrahedron 2009, 65, 4124-4129. For methods involving β-unsubstituted vinyl ketones that provide from poor to moderate ee, see the following. Al-catalyzed addition of nitroesters:
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Tetrahedron
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Dong, L.-T.1
Lu, R.-J.2
Du, Q.-S.3
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Liu, S.-P.5
Xuan, Y.-N.6
Yan, M.7
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17
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Peptide-catalyzed additions of a-nitroketones
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(h) Keller, E.; Veldman, N.; Spek, A. L.; Feringa, B. L. Tetrahedron: Asymmetry 1997, 8, 3403-3413. Peptide-catalyzed additions of a-nitroketones:
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Tetrahedron: Asymmetry
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Keller, E.1
Veldman, N.2
Spek, A.L.3
Feringa, B.L.4
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18
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33846912717
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(i) Linton, B. R.; Reutershand, R. H.; Aderman, C. M.; Richardson, E. A.; Brownell, K. R.; Ashley, C. W.; Evans, C. A.; Miller, S. J. Tetrahedron Lett. 2007, 48, 1993-1997.
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Linton, B.R.1
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Ashley, C.W.6
Evans, C.A.7
Miller, S.J.8
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19
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53849128905
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Conjugate additions of prochiral nitroalkanes to non-carbonyl Michael acceptors promoted by bifunctional thiourea organocatalysts. To nitroalkenes: (a)
-
Conjugate additions of prochiral nitroalkanes to non-carbonyl Michael acceptors promoted by bifunctional thiourea organocatalysts. To nitroalkenes: (a) Rabalakos, C.; Wulff, W. J. Am. Chem. Soc. 2008, 130, 13524-13525.
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To vinyl sulfones
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(b) Dong, X.-Q.; Teng, H.-L.; Wang, C.-J. Org. Lett. 2009, 11, 1265-1268. To vinyl sulfones:
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Dong, X.-Q.1
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0041365865
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For exceptions using preformed silyl nitronates, see: (a)
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For exceptions using preformed silyl nitronates, see: (a) Ooi, T.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 9022-9023.
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(b) Ooi, T.; Fujioka, S.; Maruoka, K. J. Am. Chem. Soc. 2004, 126, 11790-11791.
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0035831972
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For a review on remote stereocontrol, see
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For a review on remote stereocontrol, see: Mikami, K.; Shimizu, M.; Zhang, H.-C.; Maryanoff, B. E. Tetrahedron 2001, 57, 2917-2951.
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Mikami, K.1
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25
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17244368581
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-
For conjugate addition of prochiral nitroalkanes (R ≠ H) to selected chiral acrylate systems, leading to 70:30 or lower dr, see
-
For conjugate addition of prochiral nitroalkanes (R ≠ H) to selected chiral acrylate systems, leading to 70:30 or lower dr, see: Ballini, R.; Fiorini, D.; Palmieri, A.; Petrini, M. Lett. Org. Chem. 2004, 1, 335-339.
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0037019707
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(a) Palomo, C.; Oiarbide, M.; García, J. M.; González, A.; Lecumberri, A.; Linden, A. J. Am. Chem. Soc. 2002, 124, 10288-10289.
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(b) Palomo, C.; Oiarbide, M.; Arceo, E.; García, J. M.; López, R.; González, A.; Linden, A. Angew. Chem., Int. Ed. 2005, 44, 6187-6190.
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54849408611
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(c) Palomo, C.; Oiarbide, M.; García, J. M.; Banuelos, P.; Odriozola, J. M.; Razkin, J.; Linden, A. Org. Lett. 2008, 10, 2637-2640.
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0037073238
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For the concept of, and inherent problems associated with, double activation of substrates in the context of enantioselective catalysis, see
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For the concept of, and inherent problems associated with, double activation of substrates in the context of enantioselective catalysis, see: Itoh, K.; Kanemasa, S. J. Am. Chem. Soc. 2002, 124, 13394-13395.
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Itoh, K.1
Kanemasa, S.2
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30
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69449105431
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Other cyclic amines led to comparable results (N-methyl pyrrolidine, dr = 97/3; N-methyl morpholine, dr = 95/5)
-
Other cyclic amines led to comparable results (N-methyl pyrrolidine, dr = 97/3; N-methyl morpholine, dr = 95/5).
-
-
-
-
31
-
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69449100846
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2NEt) are employed at temperatures above 0°C
-
2NEt) are employed at temperatures above 0°C.
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32
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0000068548
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(a) Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1998, 63, 5483-5488.
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(c) Steinhoff, B. A.; King, A. E.; Stahl, S. S. J. Org. Chem. 2006, 71, 1861-1868.
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0024394570
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Usual carboxy-protecting groups fail with γ-amino acids because of their high tendency to lactamize spontaneously. See, for instance: (a)
-
Usual carboxy-protecting groups fail with γ-amino acids because of their high tendency to lactamize spontaneously. See, for instance: (a) Pettit, G. R.; Singh, S. B.; Hogan, F.; Lloyd-Williams, P.; Herald, D. L.; Burkett, D. D.; Clewlow, P. J. J. Am. Chem. Soc. 1989, 111, 5463-5465.
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39
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69449104874
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2 (2 equiv of Nmethylpiperidine, rt, 24 h, 0% conversion)
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2 (2 equiv of Nmethylpiperidine, rt, 24 h, 0% conversion).
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