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25
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84872274587
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note
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From a model study using chiral lactaldehyde TBS ether and the alkyne (S)-4, we found that a combination of the (R)-aldehyde and (S)-4 provided better yield and selectivity than that of (S)-aldehyde and (S)-4.
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26
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37049042197
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The stereochemistry of the benzylidene acetal was determined by an empirical rule (Baggett, N.; Buck, K. W.; Foster, A. B.; Randall, M. H.; Webber, J. M. J. Chem. Soc. 1965, 3394-3440).
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J. Chem. Soc.
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Baggett, N.1
Buck, K.W.2
Foster, A.B.3
Randall, M.H.4
Webber, J.M.5
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27
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84872272643
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note
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The diastereomeric ratio based on the benzylidene acetal for 8a and 8b was almost same as the ratio of 7a and 7b used.
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29
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0023180583
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(b) Hirama, M.; Shigemoto, T.; Ito, S. J. Org. Chem. 1987, 52, 3342-3346.
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Hirama, M.1
Shigemoto, T.2
Ito, S.3
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30
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84872263490
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note
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1H NMR spectral data of the syn adducts 8a appeared upfield by 0.1-0.2 ppm from those in the anti adducts 8b. On the other hand, the signals of the OH proton in the syn adducts appeared downfield by 0.1-0.2 ppm from that in the anti adducts. The shifts were consistent for each compound in this series.
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33
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84872263772
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note
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An attempt to obtain 10b via tosylation of 8a followed by simultaneous reduction of the triple bond and the benzylidene acetal failed presumably due to hydrogenolysis of the tosyl group.
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34
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0030752370
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and references therein
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Koert, U.; Stein, M.; Wagner, H. Chem. Eur. J. 1997, 3, 1170-1180 and references therein.
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Chem. Eur. J.
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Koert, U.1
Stein, M.2
Wagner, H.3
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