-
1
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32644443321
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Though largely attributed to Würtz, the aldol reaction was reported first by Borodin: (a) von Richter, V. Ber. Deut. Chem. Ges. 1869, 2, 552 (Borodin's earliest results are cited in this article).
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Von Richter, V.1
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6
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0000244085
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For selected reviews on stereoselective aldol additions, see: (a) Heathcock, C. H. Science 1981, 214, 395.
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Heathcock, C.H.1
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8
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0001924336
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(c) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
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Evans, D.A.1
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9
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0034678591
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(d) Machajewski, T. D.; Wong, C.-H. Angew. Chem., Int. Ed. 2000, 39, 1352.
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Machajewski, T.D.1
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1642386775
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(e) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Soc. Rev. 2004, 33, 65.
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Palomo, C.1
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Garcia, J.M.3
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11
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32644441427
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note
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3- enolate.
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-
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12
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0001622033
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(a) Velluz, L.; Valls, J.; Nomine, G. Angew. Chem., Int. Ed. Engl. 1965, 4, 181.
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Velluz, L.1
Valls, J.2
Nomine, G.3
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16
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0000617094
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Stork, G.; Rosen, P.; Goldman, N. L. J. Am. Chem. Soc. 1961, 83, 2965.
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Stork, G.1
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0001632979
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(b) Stork, G.; Rosen, P.; Goldman, N.; Coombs, R. V.; Tsuji, J. J. Am. Chem. Soc. 1965, 87, 275.
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Tsuji, J.5
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18
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0036291572
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For reviews encompassing catalytic reductive aldol coupling, see: (a) Motherwell, W. B. Pure Appl. Chem. 2002, 74, 135.
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Motherwell, W.B.1
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(c) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. Chemtracts 2003, 16, 554.
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Jang, H.-Y.1
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0034803441
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(b) Baik, T.-G.; Luis, A. L.; Wang, L.-C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112.
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Baik, T.-G.1
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26
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0037077589
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(c) Wang, L.-C.; Jang, H.-Y.; Roh, Y.; Lynch, V.; Schultz, A. J.; Wang, X.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 9448.
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Wang, L.-C.1
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Lynch, V.4
Schultz, A.J.5
Wang, X.6
Krische, M.J.7
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27
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0000191874
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For rhodium catalyzed reductive aldol couplings mediated by silane, see: (a) Revis, A.; Hilty, T. K. Tetrahedron Lett. 1987, 28, 4809.
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(b) Matsuda, I.; Takahashi, K.; Sata, S. Tetrahedron Lett. 1990, 31, 5331.
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(d) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J. Am. Chem. Soc. 2000, 122, 4528.
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Taylor, S.J.1
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(e) Emiabata-Smith, D.; McKillop, A.; Mills, C.; Motherwell, W. B.; Whitehead, A. J. Synlett 2001, 1302.
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Emiabata-Smith, D.1
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Whitehead, A.J.5
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(f) Freiria, M.; Whitehead, A. J.; Tocher, D. A.; Motherwell, W. B. Tetrahedron 2004, 60, 2673.
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Freiria, M.1
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Motherwell, W.B.4
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(h) Nishiyama, H.; Siomi, T.; Tsuchiya, Y.; Matsuda, I. J. Am. Chem. Soc. 2005, 127, 6972.
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Nishiyama, H.1
Siomi, T.2
Tsuchiya, Y.3
Matsuda, I.4
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35
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0037176242
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For rhodium catalyzed reductive aldol couplings mediated by hydrogen, see: (a) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156.
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Jang, H.-Y.1
Huddleston, R.R.2
Krische, M.J.3
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1242285016
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(d) Marriner, G. A.; Garner, S. A.; Jang, H.-Y.; Krische, M. J. J. Org. Chem. 2004, 69, 1380.
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Krische, M.J.4
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39
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0001494417
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For reductive aldol couplings catalyzed by other metals, see the following references. (a) Indium: Zhao, C.-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829.
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Zhao, C.-X.1
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Taylor, S.J.3
Morken, J.P.4
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40
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(b) Palladium: Kiyooka, S.; Shimizu, A.; Torii, S. Tetrahedron Lett. 1998, 39, 5237.
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Kiyooka, S.1
Shimizu, A.2
Torii, S.3
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0033548542
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(c) Copper: Ooi, T.; Doda, K.; Sakai, D.; Maruoka, K. Tetrahedron Lett. 1999, 40, 2133.
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Ooi, T.1
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Maruoka, K.4
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4544247135
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(e) Indium: Miura, K.; Yamada, Y.; Tomita, M.; Hosomi, A. Synlett 2004, 1985.
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Miura, K.1
Yamada, Y.2
Tomita, M.3
Hosomi, A.4
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47
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32644448063
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note
-
As a point of reference, the lithium Z(O)-enolate of 3-pentanone aldolizes with benzaldehyde under kinetically controlled conditions to provide a 9:1 syn/anti-ratio. Upon equilibration, a 44:56 syn/anti ratio results. For further examples, see ref 3a-c.
-
-
-
-
50
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32644445896
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note
-
The stereochemical assignment of 10a is based upon single crystal X-ray diffraction analysis of the corresponding 3,5-dinitrobenzoate. The 8:1 diastereomeric ratio refers to the major isomer versus all other isomers combined.
-
-
-
-
51
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32644437559
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note
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Enones constrained in the s-trans configuration, such as cyclohexenone, do not participate in reductive coupling.
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-
-
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52
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32644446608
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note
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High levels of diastereoselectivity do not preclude reversible aldolization, provided aldolization proceeds with sufficiently high levels of kinetic stereoselectivity.
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