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For isolation of the pinnaic acids, see
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The addition of dimethyl sulfide to cyclohexenone in the presence of TMSOTf is 1,4-selective and reversible. The silyloxysulfonium salt produced is thermally unstable above -40 °C. At -20 °C the equilibrium lies entirely on the side of the cyclohexenone
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The addition of dimethyl sulfide to cyclohexenone in the presence of TMSOTf is 1,4-selective and reversible. The silyloxysulfonium salt produced is thermally unstable above -40 °C. At -20 °C the equilibrium lies entirely on the side of the cyclohexenone: (a) Kim, S.; Park, J. H.; Kim, Y. G.; Lee, J. M. J. Chem. Soc., Chem. Commun. 1993, 1188.
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For a review on stereochemistry of nucleophilic addition to aminals using this auxiliary, see
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0022517466
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The following Lewis acids and nucleophile combinations were screened for the MBH-type reaction without success: (a) HCl
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The following Lewis acids and nucleophile combinations were screened for the MBH-type reaction without success: (a) HCl: Melching, K. H.; Hiemstra, H.; Klaver, W. J.; Speckamp, W. N. Tetrahedron Lett. 1986, 27, 4799.
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TiCl4 + Bu4NI
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77955375351
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We were not able to obtain crystals of the 5,5-spirocycle for analysis by X-ray diffraction, and we were unsuccessful in finding NOE correlations to assign its stereochemistry. The spirocentre stereochemistry is therefore not known in this case
-
We were not able to obtain crystals of the 5,5-spirocycle for analysis by X-ray diffraction, and we were unsuccessful in finding NOE correlations to assign its stereochemistry. The spirocentre stereochemistry is therefore not known in this case.
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41
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0021947264
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For α,β-unsaturated aldehyde reduction, see
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For Birch reduction, see ref 7j
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(b) For Birch reduction, see ref 7j.
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43
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49949128203
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The original paper concerns the effect of conformation of a stereocentre a to a carbonyl group on facial selectivity of nucleophilic addition to the carbonyl
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(a) The original paper concerns the effect of conformation of a stereocentre a to a carbonyl group on facial selectivity of nucleophilic addition to the carbonyl: Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199.
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