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Selected recent examples: (a) Barker, T. J.; Jarvo, E. R. Org. Lett. 2009, 11, 1047-1049.
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Initial discovery using allylsilanes: (a) Hosomi, A.; Sakurai, H. J. Am. Chem. Soc. 1977, 99, 1673-1675. Allylstannanes:
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Conjugate allylation of nitroalkenes: (a) Shen, K.-H.; Liu, J.-T.; Wu, Y.-R.; Yao, C.-F. Synth. Commun. 2007, 37, 3677-3687.
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Uno, H.1
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38649130639
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For recent examples of 1,2-allylation of enals and enones using allyltin reagents, see: a
-
For recent examples of 1,2-allylation of enals and enones using allyltin reagents, see: (a) Zhang, T.; Shi, M.; Zhao, M. Tetrahedron 2008, 64, 2412-2418.
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(2008)
Tetrahedron
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Zhang, T.1
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33646768210
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Enones
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(b) Lingaiah, B. V.; Ezikiel, G.; Yakaiah, T.; Reddy, G. V.; Rao, P. S. Tetrahedron Lett. 2006, 47, 4315-1318. Enones:
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Lingaiah, B.V.1
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(d) Teo, Y.-C.; Goh, J.-D.; Loh, T.-P. Org. Lett. 2005, 7, 2743-2745.
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Teo, Y.-C.1
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Loh, T.-P.3
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23
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0030790917
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Conjugate allylation of cinnamaldehyde with allyllithium in the presence of a bulky aluminum phenoxide reagent has been reported: Ooi, T, Kondo, Y, Maruoka, K. Angew. Chem, Int. Ed. Engl. 1997, 36, 1183-1185
-
Conjugate allylation of cinnamaldehyde with allyllithium in the presence of a bulky aluminum phenoxide reagent has been reported: Ooi, T.; Kondo, Y.; Maruoka, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 1183-1185.
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-
-
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24
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0142120599
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Conjugate allylation of enones with catalytic indium and excess TMSCl: Lee, P. H.; Seomoon, D.; Kim, S.; Nagaiah, K.; Damle, S. V.; Lee, K. Synthesis 2003, 2189-2193.
-
Conjugate allylation of enones with catalytic indium and excess TMSCl: Lee, P. H.; Seomoon, D.; Kim, S.; Nagaiah, K.; Damle, S. V.; Lee, K. Synthesis 2003, 2189-2193.
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25
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58149147071
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(a) Shaghafi, M. B.; Kohn, B. L.; Jarvo, E. R. Org. Lett. 2008, 10, 4743-4746.
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(b) Waetzig, J. D.; Swift, E. C.; Jarvo, E. R. Tetrahedron 2009, 65, 3197-3201.
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27
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0028102045
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Isolated examples of conjugate allylation in the presence of Lewis acids to alkylidene Meldrum's acids containing metallated dienes have been reported, see: a
-
Isolated examples of conjugate allylation in the presence of Lewis acids to alkylidene Meldrum's acids containing metallated dienes have been reported, see: (a) Wada, C. K.; Roush, W. R. Tetrahedron Lett. 1994, 35, 7351-7354.
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(1994)
Tetrahedron Lett
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Wada, C.K.1
Roush, W.R.2
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28
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0001039117
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For an intramolecular example, see
-
(b) Paley, R. S.; Estroff, L. A.; Gauguet, J.-M.; Hunt, D. K.; Newlin, R. C. Org. Lett. 2000, 2, 365-368. For an intramolecular example, see:
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Paley, R.S.1
Estroff, L.A.2
Gauguet, J.-M.3
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Dumas, A. M.; Seed, A.; Zorzitto, A. K.; Fillion, E. Tetrahedron Lett. 2007, 48, 7072-7074.
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Dumas, A.M.1
Seed, A.2
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Fillion, E.4
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31
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41649119612
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Alkylidene Meldrum's acids are significantly more electrophilic than the corresponding diethyl alkylidenemalonates, see
-
Alkylidene Meldrum's acids are significantly more electrophilic than the corresponding diethyl alkylidenemalonates, see: Kaumanns, O.; Mayr, H. J. Org. Chem. 2008, 73, 2738-2745.
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J. Org. Chem
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Kaumanns, O.1
Mayr, H.2
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32
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41649097012
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For transformations into arylketones, see: a
-
For transformations into arylketones, see: (a) Fillion, E.; Dumas, A. M. J. Org. Chem. 2008, 73, 2920-2923.
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(b) Fillion, E.; Fishlock, D.; Wilsily, A.; Goll, J. M. J. Org. Chem. 2005, 70, 1316-1327.
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J. Org. Chem
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Fillion, E.1
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Goll, J.M.4
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36
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41149101973
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For reviews on transformations of Meldrum's acid derivatives, see: a
-
For reviews on transformations of Meldrum's acid derivatives, see: (a) Ivanov, A. S. Chem. Soc. Rev. 2008, 37, 789-811.
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Mayr, H.; Bug, T.; Gotta, M. F.; Hering, N.; Irrgang, B.; Janker, B.; Kempf, B.; Loos, R.; Ofial, A. R.; Remennikov, G.; Schimmel, H. J. Am Chem. Soc. 2001, 123, 9500-9512.
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Mayr, H.1
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Kempf, B.7
Loos, R.8
Ofial, A.R.9
Remennikov, G.10
Schimmel, H.11
-
41
-
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66149091078
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The initial product formed by allylation is a triphenyltin enolate of Meldrum's acid that is protonated by acidic workup. See Supporting Information.
-
The initial product formed by allylation is a triphenyltin enolate of Meldrum's acid that is protonated by acidic workup. See Supporting Information.
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-
-
-
42
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34447295387
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Fujimori, S.; Carreira, E. M. Angew. Chem., Int. Ed. 2007, 46, 4964-4967.
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Fujimori, S.1
Carreira, E.M.2
-
43
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0033550196
-
-
For other examples of diastereselective conjugate allylation not found in refs 2 and 3, see: a
-
For other examples of diastereselective conjugate allylation not found in refs 2 and 3, see: (a) Groaning, M. D.; Meyers, A. I. Tetrahedron Lett. 1999, 40, 8071-8074.
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(1999)
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Groaning, M.D.1
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(b) Sato, M.; Aoyagi, S.; Yago, S.; Kibayashi, C. Tetrahedron Lett. 1996, 37, 9063-9066.
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Sato, M.1
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Kibayashi, C.4
-
46
-
-
0034627379
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-
For conjugate addition of indole to 1q and 1r formed in situ, see: (a) Boisbrun, M.; Kovács-Kulyassa, Á.; Jeannin, L.; Sapi, J.; Toupet, L.; Laronze, J.-Y. Tetrahedron Lett. 2000, 41, 9771-9775.
-
For conjugate addition of indole to 1q and 1r formed in situ, see: (a) Boisbrun, M.; Kovács-Kulyassa, Á.; Jeannin, L.; Sapi, J.; Toupet, L.; Laronze, J.-Y. Tetrahedron Lett. 2000, 41, 9771-9775.
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-
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47
-
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27644473168
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(b) Dardennes, E.; Kovács-Kulyassa, A.; Boisbrun, M.; Petermann, C.; Laronze, J.-Y.; Sapi, J. Tetrahedron: Asymmetry 2005, 16, 1329-1339.
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Tetrahedron: Asymmetry
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Dardennes, E.1
Kovács-Kulyassa, A.2
Boisbrun, M.3
Petermann, C.4
Laronze, J.-Y.5
Sapi, J.6
-
48
-
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66149112072
-
-
Relative stereochemistry was determined by analysis of coupling constants and proceeds with the same facial selectivity as the addition of indole ref 22
-
Relative stereochemistry was determined by analysis of coupling constants and proceeds with the same facial selectivity as the addition of indole (ref 22).
-
-
-
-
51
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33845949270
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Similar products have been obtained by the reaction of alkylidene Meldrum's acids with butadiene sulfone: Fillion, E.; Dumas, A. M.; Hogg, S. A. J. Org. Chem. 2006, 71, 9899-9902.
-
Similar products have been obtained by the reaction of alkylidene Meldrum's acids with butadiene sulfone: Fillion, E.; Dumas, A. M.; Hogg, S. A. J. Org. Chem. 2006, 71, 9899-9902.
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52
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66149090692
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See Supporting Information for details
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See Supporting Information for details.
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