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1
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0003866888
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For reviews on polyketide and polypropionate natural products, see: a, Ellis Horwood: Chichester
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For reviews on polyketide and polypropionate natural products, see: (a) O'Hagan, D. The Polyketide Metabolites; Ellis Horwood: Chichester, 1991.
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4
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61349135295
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Höfle, G.; Reichenbach, H.; Irschik, H.; Schummer, D. German Patent DE 196 30 980 Al: 1-7 (5.2. 1998).
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(a) Höfle, G.; Reichenbach, H.; Irschik, H.; Schummer, D. German Patent DE 196 30 980 Al: 1-7 (5.2. 1998).
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For recent reviews, see: a
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For recent reviews, see: (a) Yeung, K.-S.; Paterson, I. Chem. Rev. 2005, 105, 4237.
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(b) Schetter, B.; Mahrwald, R. Angew. Chem., Int. Ed. 2006, 45, 7506.
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Schetter, B.1
Mahrwald, R.2
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8
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61349181689
-
-
According to the (1,n)-nomenclature, 1 denotes the newly formed stereogenic center, while n stands for the pre-existing chiral center.
-
According to the (1,n)-nomenclature, 1 denotes the newly formed stereogenic center, while n stands for the pre-existing chiral center.
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-
-
-
9
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61349129912
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For a leading reference on substrate-controlled aldol reactions of enolates bearing different substitution patterns as compared to the one discussed herein, see ref 4b and Braun, M. In Modern Aldol Reactions; Mahrwald, R, Ed, Wiley-VCH: Weinheim, 2004; pp 1-61
-
For a leading reference on substrate-controlled aldol reactions of enolates bearing different substitution patterns as compared to the one discussed herein, see ref 4b and Braun, M. In Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, 2004; pp 1-61.
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-
-
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10
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0012876697
-
-
For selected references of aldol additions with substrate control of ethyl ketones which are structurally related to 4, see: (a) McCarthy, P, Kageyama, M. J. Org. Chem. 1987, 52, 4681
-
For selected references of aldol additions with substrate control of ethyl ketones which are structurally related to 4, see: (a) McCarthy, P.; Kageyama, M. J. Org. Chem. 1987, 52, 4681.
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11
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84958315401
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(b) Evans, D. A.; Rieger, D. L.; Bilodeau, M. T.; Urpi, F. J. Am. Chem, Soc. 1991, 113, 1047.
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Bilodeau, M.T.3
Urpi, F.4
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(c) Gustin, D. J.; VanNieuwenhze, M. S.; Roush, W. R. Tetrahedron Lett. 1995, 36, 3447.
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Gustin, D.J.1
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13
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(d) Evans, D. A.; Dart, M. J.; Duffy, J. L.; Rieger, D. L. J. Am. Chem. Soc. 1995, 117, 9073.
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Dart, M.J.2
Duffy, J.L.3
Rieger, D.L.4
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14
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(e) Evans, D. A.; Cote, B.; Coleman, P. J.; Connell, B. T. J. Am. Chem. Soc. 2003, 125, 10893.
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Evans, D.A.1
Cote, B.2
Coleman, P.J.3
Connell, B.T.4
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15
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0025053296
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For selected reference of aldol additions with substrate control from chiral methyl ketones, which are structurally related to 4, see: (a) Evans, D. A.; Gage, J. R. Tetrahedron Lett. 1990, 31, 6129.
-
For selected reference of aldol additions with substrate control from chiral methyl ketones, which are structurally related to 4, see: (a) Evans, D. A.; Gage, J. R. Tetrahedron Lett. 1990, 31, 6129.
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16
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0029058338
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(b) Gustin, D. J.; VanNieuwenhze, M. S.; Roush, W. R. Tetrahedron Lett. 1995, 36, 3443.
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(c) Paterson, I.; Gibson, K. R.; Oballa, R. M. Tetrahedron Lett. 1996, 37, 8585.
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Paterson, I.1
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(d) Evans, D. A.; Coleman, P. J.; Cote, B. J. Org. Chem. 1997, 62, 788.
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Cote, B.3
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(e) Paterson, I.; Delgado, O.; Florence, G. J.; Lyothier, I.; Scott, J. P.; Sereinig, N. Org. Lett. 2003, 5, 35.
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Paterson, I.1
Delgado, O.2
Florence, G.J.3
Lyothier, I.4
Scott, J.P.5
Sereinig, N.6
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21
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0001790298
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For a review on asymmetric boron-mediated aldol reactions, see
-
For a review on asymmetric boron-mediated aldol reactions, see: Cowden, C. J.; Paterson, I. Org. React, 1997, 51, 1.
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(1997)
Org. React
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Cowden, C.J.1
Paterson, I.2
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22
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0000784039
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For leading references on the stereochemical influence of the α-and β-chiral center of the aldehyde in aldol reactions, see: (a) Roush, W. R. J. Org. Chem. 1991, 56, 4151
-
For leading references on the stereochemical influence of the α-and β-chiral center of the aldehyde in aldol reactions, see: (a) Roush, W. R. J. Org. Chem. 1991, 56, 4151.
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24
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15844376790
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(c) Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang. M. G. J. Am. Chem. Soc. 1996, 118, 4322.
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Dart, M.J.2
Duffy, J.L.3
Yang, M.G.4
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25
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0030590403
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For recent examples of diversity-oriented polyketide library synthesis, see: a
-
For recent examples of diversity-oriented polyketide library synthesis, see: (a) Reggelin, M.; Brenig, V. Tetrahedron Lett. 1996, 6851.
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(1996)
Tetrahedron Lett
, pp. 6851
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Reggelin, M.1
Brenig, V.2
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4544365737
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(c) Barun, O.; Sommer, S.; Waldmann, H. Angew. Chem., Int. Ed. 2004, 43, 3195.
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Angew. Chem., Int. Ed
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Waldmann, H.3
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(d) Kesavan, S.; Su, Q.; Shao, J.; Porco, J. A., Jr.; Panek, J. S. Org. Lett. 2005, 7, 4435.
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Org. Lett
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Panek, J.S.5
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(e) Shang, S.; Iwadare, H.; Macks, D. E.; Ambrosini, L. M.; Tan, D. S. Org. Lett. 2007, 9, 1895.
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Org. Lett
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Ambrosini, L.M.4
Tan, D.S.5
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30
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0344137670
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For diversity oriented aldol-couplings of α-chiral silyloxy-ketones, see
-
For diversity oriented aldol-couplings of α-chiral silyloxy-ketones, see: Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. T. J. Org, Chem. 1996, 56, 2499.
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(1996)
J. Org, Chem
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Van Draanen, N.A.1
Arseniyadis, S.2
Crimmins, M.T.3
Heathcock, C.T.4
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31
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4344573922
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For an example, see
-
For an example, see: Paterson, I.; Britton, R.; Ashton, K.; Knust, H.; Stafford, J. Proc. Nat. Acad. Sci. U.S.A. 2004, 101, 11986.
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(2004)
Proc. Nat. Acad. Sci. U.S.A
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Paterson, I.1
Britton, R.2
Ashton, K.3
Knust, H.4
Stafford, J.5
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34
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0026553351
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(c) Evans, D. A.; Ng, H. P.; Clark, S.; Rieger, D. L. Tetrahedron 1992, 48, 2127.
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(1992)
Tetrahedron
, vol.48
, pp. 2127
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-
Evans, D.A.1
Ng, H.P.2
Clark, S.3
Rieger, D.L.4
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35
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61349136770
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In 1,5-anti aldol reactions of certain β-alkyxyketones, the β-substituent appears to be more influential as compared to the α-substituent; see ref 8f and literature cited therein
-
In 1,5-anti aldol reactions of certain β-alkyxyketones, the β-substituent appears to be more influential as compared to the α-substituent; see ref 8f and literature cited therein.
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-
-
-
36
-
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61349090940
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Selection of 3 and 4 was based on preliminary studies on the configurational assignment of etnangien in our own laboratories.
-
Selection of 3 and 4 was based on preliminary studies on the configurational assignment of etnangien in our own laboratories.
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-
-
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37
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61349110558
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This noncyclic transition state is in agreement with that proposed by Evans for a boron-mediated aldol reaction.14c For titanium-mediated aldol couplings, a different noncyclic model has been discussed.7b
-
7b
-
-
-
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39
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61349086540
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Mukayiama-type aldol reactions were not evaluated within this study because of practicality, as they require separate silyl-enol-ether formation
-
Mukayiama-type aldol reactions were not evaluated within this study because of practicality, as they require separate silyl-enol-ether formation.
-
-
-
-
40
-
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61349180002
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-
Analogous boron9 and titanium7b gave lower π-face selectivity and/ or proceeded with lower yields
-
7b gave lower π-face selectivity and/ or proceeded with lower yields.
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-
-
-
41
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0000739599
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Tin enolates were first introduced by Mukaiyama: Mukaiyama, T.; Iwasawa, N.; Stevens, R. W.; Haga, T. Tetrahedron 1984, 40, 1381.
-
Tin enolates were first introduced by Mukaiyama: Mukaiyama, T.; Iwasawa, N.; Stevens, R. W.; Haga, T. Tetrahedron 1984, 40, 1381.
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-
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42
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61349116032
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In all cases, dr refers to the diastereomeric ratio of the 1,4-syn to the 1,4-anti aldol products
-
In all cases, dr refers to the diastereomeric ratio of the 1,4-syn to the 1,4-anti aldol products.
-
-
-
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43
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11844259698
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For a leading reference on titanium-mediated aldol reactions, see:, Mahrwald, R, Ed, Wiley-VCH: Weinheim
-
For a leading reference on titanium-mediated aldol reactions, see: Ghosh, A. K.; Shevlin, M. In Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, 2004; pp 63-125.
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(2004)
Modern Aldol Reactions
, pp. 63-125
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Ghosh, A.K.1
Shevlin, M.2
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0027729991
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Evans, D. A.; Ng, H. P.; Rieger, D. L. J. Am. Chem. Soc. 1993, 115, 11446.
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J. Am. Chem. Soc
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, pp. 11446
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Evans, D.A.1
Ng, H.P.2
Rieger, D.L.3
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45
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61349163459
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For good stereoselectivities, short reaction times were beneficial. 7c
-
7c
-
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46
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0030894922
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Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 523.
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Angew. Chem., Int. Ed. Engl
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Bauer, A.3
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Cordes, M.5
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11844259698
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Mahrwald, R, Ed, Wiley-VCH: Weinheim
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Schinzer, D. In Modem Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, 2004; pp 311-328.
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, pp. 311-328
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Schinzer, D.1
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Dias, L. C.; Baú, R. Z.; se Sousa, M. A.; Zukerman-Schpector, J. Org. Lett. 2002, 4, 4325.
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Dias, L. C.; Baú, R. Z.; se Sousa, M. A.; Zukerman-Schpector, J. Org. Lett. 2002, 4, 4325.
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