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General reviews on the catalytic aldol reaction: (a) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; 1999; Vol. 3, p 997. (b) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
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Catalytic enantioselective and diastereoselective non-Mukaiyama ester aldol reactions: (a) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. (b) Nelson, S. G.; Peelen, T. J.; Wan, Z. J. Am. Chem. Soc. 1999, 121, 9742. (c) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J. Am. Chem. Soc. 2000, 122, 4528. (d) Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392.
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Catalytic enantioselective and diastereoselective non-Mukaiyama ester aldol reactions: (a) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. (b) Nelson, S. G.; Peelen, T. J.; Wan, Z. J. Am. Chem. Soc. 1999, 121, 9742. (c) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J. Am. Chem. Soc. 2000, 122, 4528. (d) Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392.
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Catalytic enantioselective and diastereoselective non-Mukaiyama ester aldol reactions: (a) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. (b) Nelson, S. G.; Peelen, T. J.; Wan, Z. J. Am. Chem. Soc. 1999, 121, 9742. (c) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J. Am. Chem. Soc. 2000, 122, 4528. (d) Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392.
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Recent examples of β-hydroxyketones and β-hydroxyaldehydes as products of direct aldol reactions: (a) Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12003. (b) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (c) Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168. (d) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798.
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Recent examples of β-hydroxyketones and β-hydroxyaldehydes as products of direct aldol reactions: (a) Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12003. (b) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (c) Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168. (d) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798.
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Recent examples of β-hydroxyketones and β-hydroxyaldehydes as products of direct aldol reactions: (a) Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12003. (b) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (c) Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168. (d) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798.
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Recent examples of β-hydroxyketones and β-hydroxyaldehydes as products of direct aldol reactions: (a) Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12003. (b) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (c) Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168. (d) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798.
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15
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12444273113
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note
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2O is tolerated.
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17
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84969808662
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(b) Brooks, D. W.; Lu, L. D. L.; Masamune, S. Angew. Chem. Int. Ed. Engl. 1979, 18, 72.
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(b) Sakai, N.; Sorde, N.; Matile, S. Molecules 2001, 6, 845.
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0000289429
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(2) was prepared in one step from malonic acid and benzyl mercaptan by following the procedure in Imamoto, T.; Masahito, K.; Yokoyama, M. Bull. Chem. Soc. Jpn. 1982, 55, 2303.
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12444274123
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note
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The same results were obtained when the reactions were performed under an atmosphere of argon with rigorous exclusion of water.
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23
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0036703508
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For a recent review on stereoselective reactions, including aldol, in the presence of water, see: Lindstrom, U. M. Chem. Rev. 2002, 102, 2751.
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0001589290
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For metal-catalyzed decarboxylation of malonic acids and malonic acid half oxyesters, see: (a) Toussaint, O.; Capdevielle, P.; Maumy, M. Synthesis 1986, 12, 1029. (b) Darensbourg, D. J.; Holtcamp, M. W.; Khandelwal, B.; Reibenspies, J. H. Inorg. Chem. 1994, 33, 531.
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26
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33751157521
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For metal-catalyzed decarboxylation of malonic acids and malonic acid half oxyesters, see: (a) Toussaint, O.; Capdevielle, P.; Maumy, M. Synthesis 1986, 12, 1029. (b) Darensbourg, D. J.; Holtcamp, M. W.; Khandelwal, B.; Reibenspies, J. H. Inorg. Chem. 1994, 33, 531.
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0001315449
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For an alternative role of metal salts in decarboxylation of malonic acids and malonic acid half oxyesters, see: Brunner, H.; Muller, J.; Spitzer, J. Monatsh. Chem. 1996, 127, 845.
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28
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12444262690
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note
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For a detailed description of this experiment, see the Supporting Information.
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29
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0023099216
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For a discussion of thermodynamic and kinetic properties of ATP and its role in biology, see: Westheimer, F. H. Science 1987, 235, 1173.
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Science
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Westheimer, F.H.1
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30
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12444269464
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note
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MAHTs 2 and 3 can be stored in an open vial at room temperature for months without decomposition.
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