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26
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37049103873
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26. The erythro-phenylthio alcohol (erythro-20, a mixture of two erythro-diastereomers) was converted stereospecifically to the (E)-isomer of 1 by the same treatment. This fact supports our assignments of the relative stereochemistries for threo-20 and erythro-20. For similar threo-selective addition of a hydride ion to α-phenylthio or α-methylthio ketones, see: Brownbridge, P.; Egert, E.; Hunt, P. G.; Kennard, O.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1981, 2751-2759; Shimagaki, M.; Maeda, T.; Matsuzaki, Y.; Hori, I.; Nakata, T.; Oishi, T. Tetrahedron Lett. 1984, 25, 4775-4778.
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Brownbridge, P.1
Egert, E.2
Hunt, P.G.3
Kennard, O.4
Warren, S.5
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27
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0000822952
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26. The erythro-phenylthio alcohol (erythro-20, a mixture of two erythro-diastereomers) was converted stereospecifically to the (E)-isomer of 1 by the same treatment. This fact supports our assignments of the relative stereochemistries for threo-20 and erythro-20. For similar threo-selective addition of a hydride ion to α-phenylthio or α-methylthio ketones, see: Brownbridge, P.; Egert, E.; Hunt, P. G.; Kennard, O.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1981, 2751-2759; Shimagaki, M.; Maeda, T.; Matsuzaki, Y.; Hori, I.; Nakata, T.; Oishi, T. Tetrahedron Lett. 1984, 25, 4775-4778.
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Shimagaki, M.1
Maeda, T.2
Matsuzaki, Y.3
Hori, I.4
Nakata, T.5
Oishi, T.6
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29
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85038549788
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note
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1H NMR spectra of 22a, 23, and 24. The equatorially oriented C-2 proton of 22a and 23 both appeared as a broad singlet with small unresolved couplings (at δ 3.63 and δ 4.80, respectively). On the other hand, the axially oriented C-2 proton of 24 was observed as a double doublet ( at δ 3.85, J = 12.0, 5.0 Hz).
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