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This observation is in accord with that of Heimgartner and coworkers who shwoed that when the lithium enolates derived from N-methyl-N-phenylcarboxamides were treated with diphenyl-phosphoryl azide at 0 °C the corresponding α-diazoamide was obtained as the sole reaction product, see: J. M. Villalgordo, A. Linden and H. Heimgartner, Helv. Chim. Acta, 1996, 79, 213.
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Participation of a neighbouring N-Boc group and in situ oxazolidinone formation with either a triflate or tosylate leaving group have been reported, see: Y. Nakamura, M. Hirai, K. Tamotsu, Y. Yonezawa and C. Shin, Bull. Chim. Soc. Jpn, 1995, 68, 1369.
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84988742408
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1H NMR spectra of the anti- and syn-diastereo-isomers 2 and 3 respectively showed distinct differences in coupling constans, with the C(2)-C(3) coupling constant in the syn-isomer being ∼3 Hz, while in the anti-diastereoisomer it is 7 Hz, consistent with those noted by Janda et al. (see reference 25).
-
-
-
-
65
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84988766064
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note
-
(2S,3S)-ter-Butyl 2-hydroxy-3-aminobutanoate 21 is commercially available from Evotec OAI.
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