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65549150422
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Determined by optical rotation, see Ref. 5c Unfortunately, no yields were given for the catalysis.
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23
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65549141204
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note
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We also detected the incorporation of solvent protons into the product when using deuterated methanol. Furthermore, deuterium was incorporated in a transesterification of α-hydroxythiolphenol ester 4 under standard reaction conditions. This proved that the α-hydrogen in the primary product was acidic and could easily be exchanged.
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For the use of these aminothiols as ligands in asymmetric alkenylzinc additions to aldehydes, see:
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65549130100
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note
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Prolongation of the reaction time did not further increase the product yields. Use of quinine, cinchonine and cinchonidine afforded slightly lower amounts of methyl mandelate.
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52
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34347258004
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For a review, see: Angew. Chem., Int. Ed. 2006, 45, 1496
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Cupreidine was prepared according to Deng's protocol:. Li H., Wang Y., Tang L., and Deng L. J. Am. Chem. Soc. 126 (2004) 9906
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For the synthesis of mandelic acid thiophenolester from l-mandelic acid, see:
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For the synthesis of mandelic acid thiophenolester from l-mandelic acid, see:. Yang H., and Liebeskind L.S. Org. Lett. 9 (2007) 2993
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65549136670
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note
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According to Ref. 5a, the conversion of phenylglyoxal in the presence of 5 mol % of 2-(N,N-diethylamino)ethanthiol afforded methyl mandelate in 72% yield after 12 h at room temperature. In our hands, use of 20 mol % of the same amino thiol led to a maximum yield of 60% after 48 h.
-
-
-
-
64
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0000530877
-
-
The hydrochloric salts of 2-(piperidino)ethanthiol (10c) and 2-(morpholino)ethanthiol (10d) were prepared from ethylenesulfide and the corresponding amines. See:
-
The hydrochloric salts of 2-(piperidino)ethanthiol (10c) and 2-(morpholino)ethanthiol (10d) were prepared from ethylenesulfide and the corresponding amines. See:. Snyder H.R., Stewart J.M., and Ziegler J.B. J. Am. Chem. Soc. 69 (1947) 2672
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