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35
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67649403690
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note
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In some cases the reactions of chelated enolates with aromatic aldehydes proceed with low diastereoselectivicity, probably because of the reversibility of the aldol process.
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36
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0001797240
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No epimerization of the ester 7a was observed. According to Seebach et al. LHMDS is not able to deprotonate amino acid esters except glycine and sarcosine, see: Ernst, B.; Leumann, C., Eds.; Verlag Helvetica Chimica Acta: Basel, and references cited therein
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No epimerization of the ester 7a was observed. According to Seebach et al. LHMDS is not able to deprotonate amino acid esters except glycine and sarcosine, see: Seebach, D.; Beck, A. K.; Studer, A. In Modern Synthetic Methods, Vol.7; Ernst, B.; Leumann, C., Eds.; Verlag Helvetica Chimica Acta: Basel, 1995, 1-178; and references cited therein.
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, pp. 1-178
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Seebach, D.1
Beck, A.K.2
Studer, A.3
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37
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67649405120
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note
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It should be mentioned, that NMR is not a suitable method for determination of the isomeric ratios, because in addition to the signals of the different isomers, in general a double set of signals is observed caused by rotamers (hindered rotation around the secondary amide bond).
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-
-
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41
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67649410651
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note
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2, hexanes-EtOAc).
-
-
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-
42
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67649414723
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note
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6 (397.39): C, 51.38; H, 6.56; N, 3.52. Found: C, 50.98; H, 6.37; N, 3.56.
-
-
-
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43
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67649402242
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-
note
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Unfortunately the aldol products obtained with aromatic aldehydes could not be analyzed by GC; NMR has to be used in this case. Therefore, we were not able to determine exact ratios, but the NMR spectra indicated that the isomers were formed in comparable amounts.
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