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Helmchen G., Hoffmann R.W., Mulzer J., and Schaumann E. (Eds), Georg Thieme, Stuttgart
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Braun M. In: Helmchen G., Hoffmann R.W., Mulzer J., and Schaumann E. (Eds). Houben-Weyl. Methods of Organic Chemistry. Stereoselective Synthesis Vol. E21b (1995), Georg Thieme, Stuttgart 1603-1666
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Braun, M.1
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Mahrwald R. (Ed), Wiley-VCH, Weinheim
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In: Mahrwald R. (Ed). Modern Aldol Reactions (2004), Wiley-VCH, Weinheim
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Modern Aldol Reactions
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62349099126
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Brodmann T., Lorenz M., Schäckel R., Simsek S., and Kalesse M. Synlett (2009) 174-192
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Synlett
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Brodmann, T.1
Lorenz, M.2
Schäckel, R.3
Simsek, S.4
Kalesse, M.5
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10
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73249147031
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note
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The term acetate aldol reaction refers to any aldol transformation involving unsubstituted enolates, which encompasses the reactions from acetate esters or methyl ketones.
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12
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0028853930
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In contrast to other aldol reactions that proceed through closed transition states, both chair- and boat-like transition state models have been invoked to rationalize the stereochemical outcome of such reactions. For theoretical calculations on boron-mediated aldol reactions of ethyl and methyl ketones, see:
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In contrast to other aldol reactions that proceed through closed transition states, both chair- and boat-like transition state models have been invoked to rationalize the stereochemical outcome of such reactions. For theoretical calculations on boron-mediated aldol reactions of ethyl and methyl ketones, see:. Bernardi A., Gennari C., Goodman J.M., and Paterson I. Tetrahedron: Asymmetry 6 (1995) 2613-2636
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(1995)
Tetrahedron: Asymmetry
, vol.6
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Bernardi, A.1
Gennari, C.2
Goodman, J.M.3
Paterson, I.4
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13
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39349099300
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For an insightful analysis of some key structural elements that control the stereochemical outcome of boron-mediated acetate aldol reactions, see:
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For an insightful analysis of some key structural elements that control the stereochemical outcome of boron-mediated acetate aldol reactions, see:. Paton R.S., and Goodman J.M. J. Org. Chem. 73 (2008) 1253-1263
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(2008)
J. Org. Chem.
, vol.73
, pp. 1253-1263
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Paton, R.S.1
Goodman, J.M.2
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14
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34548633472
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For recent examples illustrating the complexity of acetate aldol reactions, see:
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For recent examples illustrating the complexity of acetate aldol reactions, see:. Paterson I., Findlay A.D., and Anderson E.A. Angew. Chem., Int. Ed. 46 (2007) 6699-6702
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(2007)
Angew. Chem., Int. Ed.
, vol.46
, pp. 6699-6702
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Paterson, I.1
Findlay, A.D.2
Anderson, E.A.3
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15
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65349119947
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Fürstner A., Bouchez L.C., Morency L., Funel J.-A., Liepins V., Porée F.-H., Gilmour R., Laurich D., Beaufils F., and Tamiya M. Chem. Eur. J. 15 (2009) 3983-4010
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Fürstner, A.1
Bouchez, L.C.2
Morency, L.3
Funel, J.-A.4
Liepins, V.5
Porée, F.-H.6
Gilmour, R.7
Laurich, D.8
Beaufils, F.9
Tamiya, M.10
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16
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0000444632
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For studies on stereoselective aldol reactions from chiral α-hydroxy methyl ketones, see:
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For studies on stereoselective aldol reactions from chiral α-hydroxy methyl ketones, see:. Trost B.M., and Urabe H. J. Org. Chem. 55 (1990) 3982-3983
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(1990)
J. Org. Chem.
, vol.55
, pp. 3982-3983
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Trost, B.M.1
Urabe, H.2
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17
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0033603858
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Evans D.A., Carter P.H., Carreira E.M., Charette A.B., Prunet J.A., and Lautens M. J. Am. Chem. Soc. 121 (1999) 7540-7552
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J. Am. Chem. Soc.
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Evans, D.A.1
Carter, P.H.2
Carreira, E.M.3
Charette, A.B.4
Prunet, J.A.5
Lautens, M.6
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18
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0033615583
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Palomo C., Oiarbide M., Aizpurua J.M., González A., García J.M., Landa C., Odriozola I., and Linden A. J. Org. Chem. 64 (1999) 8193-8200
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Palomo, C.1
Oiarbide, M.2
Aizpurua, J.M.3
González, A.4
García, J.M.5
Landa, C.6
Odriozola, I.7
Linden, A.8
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21
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0003377268
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7b and:
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7b and:. Ishiyama H., Takemura T., Tsuda M., and Kobayashi J. J. Chem. Soc., Perkin Trans. 1 (1999) 1163-1166
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(1999)
J. Chem. Soc., Perkin Trans. 1
, pp. 1163-1166
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Ishiyama, H.1
Takemura, T.2
Tsuda, M.3
Kobayashi, J.4
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22
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0035813890
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Paterson I., Chen D.Y.-K., Coster M.J., Aceña J.L., Bach J., Gibson K.R., Keown L.E., Oballa R.M., Trieselmann T., Wallace D.J., Hodgson A.P., and Norcross R.D. Angew. Chem., Int. Ed. 40 (2001) 4055-4060
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(2001)
Angew. Chem., Int. Ed.
, vol.40
, pp. 4055-4060
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Paterson, I.1
Chen, D.Y.-K.2
Coster, M.J.3
Aceña, J.L.4
Bach, J.5
Gibson, K.R.6
Keown, L.E.7
Oballa, R.M.8
Trieselmann, T.9
Wallace, D.J.10
Hodgson, A.P.11
Norcross, R.D.12
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23
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0037157129
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Crimmins M.T., Katz J.D., Washburn D.G., Allwein S.P., and McAtee L.F. J. Am. Chem. Soc. 124 (2002) 5661-5663
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Crimmins, M.T.1
Katz, J.D.2
Washburn, D.G.3
Allwein, S.P.4
McAtee, L.F.5
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73249135788
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note
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The Mukaiyama aldol reaction of the leucine-derived methyl α-OTES ketone with isobutyraldehyde affords the corresponding syn aldol as a single diastereomer (dr syn/anti 98:2) but in low yield (36%).
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33749989298
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Nebot J., Figueras S., Romea P., Urpí F., and Ji Y. Tetrahedron 62 (2006) 11090-11099
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(2006)
Tetrahedron
, vol.62
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Nebot, J.1
Figueras, S.2
Romea, P.3
Urpí, F.4
Ji, Y.5
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33
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0033775342
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For the synthesis of ketones 1-3, see:
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For the synthesis of ketones 1-3, see:. Ferreró M., Galobardes M., Martín R., Montes T., Romea P., Rovira R., Urpí F., and Vilarrasa J. Synthesis (2000) 1608-1614
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(2000)
Synthesis
, pp. 1608-1614
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Ferreró, M.1
Galobardes, M.2
Martín, R.3
Montes, T.4
Romea, P.5
Rovira, R.6
Urpí, F.7
Vilarrasa, J.8
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34
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73249125143
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note
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The aldol reaction was also carried out at -94 °C. However, it turned out to be too sluggish and required longer reaction times.
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35
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73249152745
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note
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4) and concentrated. The resulting oil was analyzed by NMR and purified by flash chromatography (hexanes/EtOAc).
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36
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0001353039
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At this point, it is worth mentioning that the boron-mediated aldol reactions from mandelic-derived tert-butyldimethylsilyloxy methyl ketone provided a roughly equimolar mixture of two diastereomeric aldol adducts, which was assumed to be due to the competition between two boat-like transition states, see: Therefore, it is clear the crucial role of the metal on the transition states and the stereochemical outcome of such reactions
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At this point, it is worth mentioning that the boron-mediated aldol reactions from mandelic-derived tert-butyldimethylsilyloxy methyl ketone provided a roughly equimolar mixture of two diastereomeric aldol adducts, which was assumed to be due to the competition between two boat-like transition states, see:. Masamune S., Sato T., Kim B., and Wollmann T.A. J. Am. Chem. Soc. 108 (1986) 8279-8281 Therefore, it is clear the crucial role of the metal on the transition states and the stereochemical outcome of such reactions
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(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 8279-8281
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Masamune, S.1
Sato, T.2
Kim, B.3
Wollmann, T.A.4
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