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For a recent general review on the synthesis and applications of sulfinamides see: a
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(b) For a recent general review on the synthesis and applications of sulfinamides see: (a) Senanayake, C. H.; Krishnamurthy, D.; Lu, Z-H.; Han, Z.; Gallou, I. Aldrichimica Acta 2005, 38, 93.
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34547909035
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Hydrogenation of various imine derivatives derived from (4S)-3 provided predominantly cis product.
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Hydrogenation of various imine derivatives derived from (4S)-3 provided predominantly cis product.
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20
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s,4S)-5, 29.6 min; 7, 24.8 min; 1, 11.5 min.
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s,4S)-5, 29.6 min; 7, 24.8 min; 1, 11.5 min.
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For the asymmetric reduction of tert-butylsulfinyl imines see: a
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For the asymmetric reduction of tert-butylsulfinyl imines see: (a) Kochi, T.; Tang, T. P.; Ellman, J. A. J. Am. Chem. Soc. 2003, 125, 11276.
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37
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34547862925
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3b,4 = 8.4 Hz), 3.44 (ddd, 1H, J = 4.0, 7.6, 13.2 Hz), 2.89 (ddd, 1H, J = 4.4, 9.6, 13.2 Hz), 2.42 (s, 3H), 2.32 (m, 1H,), 2.17 (m, 1H).
-
3b,4 = 8.4 Hz), 3.44 (ddd, 1H, J = 4.0, 7.6, 13.2 Hz), 2.89 (ddd, 1H, J = 4.4, 9.6, 13.2 Hz), 2.42 (s, 3H), 2.32 (m, 1H,), 2.17 (m, 1H).
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38
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34547898557
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(R)-p-Toluene sulfinamide is listed in the Aldrich 2006 catalogue at 0.5g/ $59.40, whereas the (S)-isomer is listed at 5.0g/$126.50.
-
(R)-p-Toluene sulfinamide is listed in the Aldrich 2006 catalogue at 0.5g/ $59.40, whereas the (S)-isomer is listed at 5.0g/$126.50.
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39
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33750357957
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(a) Colyer, J. P.; Andersen, N. G.; Tedrow, J. S.; Soukup, T. S.; Faul, M. M. J. Org. Chem. 2006, 71, 6859.
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41
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34547887786
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16 when sodium borohydride was used as reducing agent in methanol as compared to more sterically demanding 9-BBN in THF. Also, sodium borohydride in THF at 0°C gave 95% conversion and reverse selectivity of 85/15 trans/cis. However, L-Selectride in THF at 0 °C gave > 99% conversion and 1/99 ratio of trans/cis.
-
16 when sodium borohydride was used as reducing agent in methanol as compared to more sterically demanding 9-BBN in THF. Also, sodium borohydride in THF at 0°C gave 95% conversion and reverse selectivity of 85/15 trans/cis. However, L-Selectride in THF at 0 °C gave > 99% conversion and 1/99 ratio of trans/cis.
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42
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0031483042
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(a) Davis, F. A.; Portonovo, P. S.; Reddy, G. V.; Zhou, P. Phosphorus, Sulfur Silicon Relat. Elem. 1997, 120, 291.
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(b) Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913.
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44
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34547889273
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-
2O, 95:5:0.05:0.01; flow rate of 0.8 mL/minute; ambient temperature; 220 nm wavelength. Approximate retention times for (1R,4S)-1, 39 min; for (1S,4S)-1, 36 min. In addition, this verified that no epimerization of the 45 center occurred during processing.
-
2O, 95:5:0.05:0.01; flow rate of 0.8 mL/minute; ambient temperature; 220 nm wavelength. Approximate retention times for (1R,4S)-1, 39 min; for (1S,4S)-1, 36 min. In addition, this verified that no epimerization of the 45 center occurred during processing.
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