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Eds.: Trost, B.M.; Fleming, I., Pergamon Press, Oxford, Ed.: Heathcock, C.H.
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1. Comprehensive Organic Chemistry, (Eds.: Trost, B.M.; Fleming, I.), Pergamon Press, Oxford, 1991, Vol. 2, (Ed.: Heathcock, C.H.):
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Comprehensive Organic Chemistry
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chapter 1.5, 133
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(a) Heathcock, C.H., chapter 1.5, pp 133; chapter 1.6 pp. 181;
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Heathcock, C.H.1
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chapter 1.6
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(a) Heathcock, C.H., chapter 1.5, pp 133; chapter 1.6 pp. 181;
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85030270774
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chapter 1.9
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(c) Paterson, I., chapter 1.9, pp. 301.
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Paterson, I.1
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6
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2. For recent reviews on this topic, see: (a) Franklin, A.S.; Paterson, I. Contemp. Org. Synth., 1994, 1, 317;
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3 Evans, D.A. in Asymmetric Synthesis (Ed.: Morrison, J.D.) Academic Press, New York, 1984, Vol. 3, p.1.
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Evans, D.A.1
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4 Oppolzer, W.; Bragg, J.; Walter, E. J. Am. Chem. Soc., 1990, 112, 2767. For a review, see: Oppolzer, W. Tetrahedron, 1987, 43, 1969.
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4 Oppolzer, W.; Bragg, J.; Walter, E. J. Am. Chem. Soc., 1990, 112, 2767. For a review, see: Oppolzer, W. Tetrahedron, 1987, 43, 1969.
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For a detailed information on aldol reactions using α-unsubstituted enolates, see
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6. For a relevant example using a diastereoselective Mukaiyama aldol reaction, see: Oppolzer, W.; Starkemann, C. Tetrahedron Lett., 1992, 33, 2439. For a detailed information on aldol reactions using α-unsubstituted enolates, see:
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Oppolzer, W.1
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(b) Braun, M. in Advances in Carbanion Chemistry (Ed.: Snieckus, V.) Jai Press, London, Vol. 1, 1992, p. 177.
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23
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84985633277
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11. Normally, lithium enolates of chiral acetates require transmetalation to achieve good diastereoselectivity, otherwise lower levels of asymmetric induction are often observed. For example, see: (a) Helmchen, G.; Leikauf, U.; Taufer-Knopfel, I. Angew. Chem. Int. Ed. Engl., 1985, 24, 874;
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13. (a) Yan, T.-H.; Hung, A.-W.; Lee, H.-C; Chang, C.-S.; Liu, W.-H. J. Org. Chem., 1995, 60, 3301;
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34
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85030277896
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note
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8b.
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35
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33751385708
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and references cited therein
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17. During the course of our investigations an example of such a reversal, unnoticed by the authors, has appeared (ref. 12). For a detailed discussion on this topic for aldol reactions with α-substituted enolates, see: (a) Pridgen, L.N.; Abdel-Magid, A.F.; Lantos, I.; Shilcrat, S.; Eggleston, D.S. J. Org. Chem., 1993, 58, 5107, and references cited therein.
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Pridgen, L.N.1
Abdel-Magid, A.F.2
Lantos, I.3
Shilcrat, S.4
Eggleston, D.S.5
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36
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85030269627
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note
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18. This uniform behaviour has been shown by different metal enolates, as reported in ref. 7, 8b, 9, 10, 11a-c and 13.
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37
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0001597804
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19. Evans, D.A.; Britton, T.C.; Ellman, J.A. Tetrahedron Lett. 1987, 28, 6141.
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Evans, D.A.1
Britton, T.C.2
Ellman, J.A.3
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39
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85030269056
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note
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21. The structure of 5g and 10 was unequivocally confirmed by X-ray crystallographic analysis. The X-ray data have been deposited at Cambridge Crystallographic Data Center.
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