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The electronic influence of remote substituents is important in oxazaborolidine-mediated reductions. (a) Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1995, 36, 9153-9156.
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4 modified by (-)-N-methylephedrine, see Iwasaki, G.; Sano, M.; Sodeoka, M.; Yoshida, K.; Shibasaki, M. J. Org. Chem. 1988, 53, 4864-4867.
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(b) Use of yeast as reductant in the preparation of 2b (99% e.e.), see Fronza, G.; Fogliato, G.; Fuganti, C.; Lanati, S.; Rallo, R.; Servi, S. Tetrahedron Lett. 1995, 36, 123-124; Fronza, G.; Fogliato, G.; Fuganti, C.; Lanati, S.; Rallo, R.; Rigoni, R.; Servi, S. Tetrahedron 1995, 51, 10231-10240. Only the absolute stereochemistry of 2b has been established unambiguously.
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Fronza, G.1
Fogliato, G.2
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(b) Use of yeast as reductant in the preparation of 2b (99% e.e.), see Fronza, G.; Fogliato, G.; Fuganti, C.; Lanati, S.; Rallo, R.; Servi, S. Tetrahedron Lett. 1995, 36, 123-124; Fronza, G.; Fogliato, G.; Fuganti, C.; Lanati, S.; Rallo, R.; Rigoni, R.; Servi, S. Tetrahedron 1995, 51, 10231-10240. Only the absolute stereochemistry of 2b has been established unambiguously.
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Fronza, G.1
Fogliato, G.2
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(c) Corey, E. J.; Shibati, S.; Bakshi, R. K. J. Org. Chem. 1988, 53, 2861-2863. For synthetic applications of 3 see ref. 2a and for a review on the use of oxazaborolidines in asymmetric synthesis, see Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475-1504.
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Mathre, D. J.; Jones, T. K.; Xavier, L. C.; Blacklock, T. J.; Reamer, R. A.; Mohan, J. J.; Turner Jones, E. T.; Hoogsteen, K.; Baum, M. W.; Grabowski, E. J. J. J. Org. Chem. 1991, 56, 751-762. Mathre, D. J.; Thompson, A. S.; Douglas, A. W.; Hoogsteen, K.; Carroll, J. D.; Corley, E. G.; Grabowski, E. J. J. J. Org. Chem. 1993, 58, 2880-2888.
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1b Emerson, W. S.; Birum, G. H.; Longley, R. I. J. Am. Chem. Soc. 1953, 72, 1312-1313;
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1c Hückel, W.; Maier, M.; Jordan, E.; Seeger, W. Liebigs Ann. Chem. 1958, 616, 46-81, Varech, D.; Ouannes, C.; Jacques, J. Bull. Soc. Chim. Fr. 1965, 32, 1662-1669;
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Stockman, R. A.; Szeto, P.; Thompson, S. H. J.; Hadley, M. S.; Lathbury, D. C.; Gallagher, T. Synlett 1996, 853-855.
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21
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0342576796
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note
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2 (0.3 mL) at -20°C. After completion of reaction (1 to 1.5 h), cold methanol (3 mL) was added and the solution was then stirred for 1 h. Concentration in vacuo followed by rapid flash chromatography (90:10 hexane:EtOAc) gave allylic alcohols 2.
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22
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0028220644
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For the effect of temperature on the efficiency of oxazaborolidine reductions, see Stone, G. B. Tetrahedron: Asymmetry 1994, 5, 465-472. For further mechanistic studies, see Douglas, A. W.; Tschaen, D. M.; Reamer, R. A.; Shi, Y. J. Tetrahedron: Asymmetry 1996, 7, 1303-1308.
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Stone, G.B.1
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23
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0030000283
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For the effect of temperature on the efficiency of oxazaborolidine reductions, see Stone, G. B. Tetrahedron: Asymmetry 1994, 5, 465-472. For further mechanistic studies, see Douglas, A. W.; Tschaen, D. M.; Reamer, R. A.; Shi, Y. J. Tetrahedron: Asymmetry 1996, 7, 1303-1308.
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Tetrahedron: Asymmetry
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Douglas, A.W.1
Tschaen, D.M.2
Reamer, R.A.3
Shi, Y.J.4
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24
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0010640653
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3) see Dale, J. A., Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549.
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Dale, J.A.1
Dull, D.L.2
Mosher, H.S.3
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25
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0024294399
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4a (also Evans, D. A. Science 1988, 240, 420) and chair transition states have been suggested for the delivery of hydride. For computational studies on the possible role of a chair transition state see Jones, D. K.; Liotta, D. C.; Shinkai, I.; Mathre, D. J. J. Org. Chem. 1993, 58, 799-781; Linney, L. P.; Self, C. R.; Williams, I. H. J. Chem. Soc., Chem. Commun. 1994, 1651-2.
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Evans, D.A.1
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26
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0001752772
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4a (also Evans, D. A. Science 1988, 240, 420) and chair transition states have been suggested for the delivery of hydride. For computational studies on the possible role of a chair transition state see Jones, D. K.; Liotta, D. C.; Shinkai, I.; Mathre, D. J. J. Org. Chem. 1993, 58, 799-781; Linney, L. P.; Self, C. R.; Williams, I. H. J. Chem. Soc., Chem. Commun. 1994, 1651-2.
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Jones, D.K.1
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Shinkai, I.3
Mathre, D.J.4
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27
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37049079876
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4a (also Evans, D. A. Science 1988, 240, 420) and chair transition states have been suggested for the delivery of hydride. For computational studies on the possible role of a chair transition state see Jones, D. K.; Liotta, D. C.; Shinkai, I.; Mathre, D. J. J. Org. Chem. 1993, 58, 799-781; Linney, L. P.; Self, C. R.; Williams, I. H. J. Chem. Soc., Chem. Commun. 1994, 1651-2.
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Linney, L.P.1
Self, C.R.2
Williams, I.H.3
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28
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0342576792
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note
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3b, the other allylic alcohols described in this paper have not previously been described in enantiomerically enriched form. All new compounds have been fully characterised.
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