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Asymmetric Synthesis of (2S,3R)- and (2S,3S)-2-Aminomethyl-3-hydroxy-3-phenylpropanoic Acids via a Chiral NiII Complex of a Schiff Base Prepared from β-Alanine and (S)-2-[-N-(N‘-benzyl)prolylamino]benzophenone

Yurii Nikolaevich Belokon 1
Yurii Nikolaevich Belokon
, 
Snieguole M Motsishkite 1
Snieguole M Motsishkite
,  , 
Svetlana A Orlova 1
Svetlana A Orlova
, 
Nikolai Sergeyevich Ikonnikov 1
Nikolai Sergeyevich Ikonnikov
,  , 
Andrei Stepanovich Batsanov 1
Andrei Stepanovich Batsanov
, 
Yuri Timofeevich Struchkov 1
Yuri Timofeevich Struchkov
10.1070/MC1992v002n03ABEH000147
Published 1992-09-30
Communication , Volume 2, Issue 3, 89-91
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Belokon Y. N. et al. Asymmetric Synthesis of (2S,3R)- and (2S,3S)-2-Aminomethyl-3-hydroxy-3-phenylpropanoic Acids via a Chiral NiII Complex of a Schiff Base Prepared from β-Alanine and (S)-2-[-N-(N‘-benzyl)prolylamino]benzophenone // Mendeleev Communications. 1992. Vol. 2. No. 3. pp. 89-91.
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Belokon Y. N., Motsishkite S. M., Maleev V. I., Orlova S. A., Ikonnikov N. S., Shamuratov E. B., Batsanov A. S., Struchkov Y. T. Asymmetric Synthesis of (2S,3R)- and (2S,3S)-2-Aminomethyl-3-hydroxy-3-phenylpropanoic Acids via a Chiral NiII Complex of a Schiff Base Prepared from β-Alanine and (S)-2-[-N-(N‘-benzyl)prolylamino]benzophenone // Mendeleev Communications. 1992. Vol. 2. No. 3. pp. 89-91.
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TY - JOUR
DO - 10.1070/MC1992v002n03ABEH000147
UR - https://mendcomm.colab.ws/publications/10.1070/MC1992v002n03ABEH000147
TI - Asymmetric Synthesis of (2S,3R)- and (2S,3S)-2-Aminomethyl-3-hydroxy-3-phenylpropanoic Acids via a Chiral NiII Complex of a Schiff Base Prepared from β-Alanine and (S)-2-[-N-(N‘-benzyl)prolylamino]benzophenone
T2 - Mendeleev Communications
AU - Belokon, Yurii Nikolaevich
AU - Motsishkite, Snieguole M
AU - Maleev, Victor Ivanovich
AU - Orlova, Svetlana A
AU - Ikonnikov, Nikolai Sergeyevich
AU - Shamuratov, Ergash Baitovich
AU - Batsanov, Andrei Stepanovich
AU - Struchkov, Yuri Timofeevich
PY - 1992
DA - 1992/09/30
PB - Mendeleev Communications
SP - 89-91
IS - 3
VL - 2
ER -
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@article{1992_Belokon,
author = {Yurii Nikolaevich Belokon and Snieguole M Motsishkite and Victor Ivanovich Maleev and Svetlana A Orlova and Nikolai Sergeyevich Ikonnikov and Ergash Baitovich Shamuratov and Andrei Stepanovich Batsanov and Yuri Timofeevich Struchkov},
title = {Asymmetric Synthesis of (2S,3R)- and (2S,3S)-2-Aminomethyl-3-hydroxy-3-phenylpropanoic Acids via a Chiral NiII Complex of a Schiff Base Prepared from β-Alanine and (S)-2-[-N-(N‘-benzyl)prolylamino]benzophenone},
journal = {Mendeleev Communications},
year = {1992},
volume = {2},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1992v002n03ABEH000147},
number = {3},
pages = {89--91},
doi = {10.1070/MC1992v002n03ABEH000147}
}
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Belokon, Yurii Nikolaevich, et al. “Asymmetric Synthesis of (2S,3R)- and (2S,3S)-2-Aminomethyl-3-hydroxy-3-phenylpropanoic Acids via a Chiral NiII Complex of a Schiff Base Prepared from β-Alanine and (S)-2-[-N-(N‘-benzyl)prolylamino]benzophenone.” Mendeleev Communications, vol. 2, no. 3, Sep. 1992, pp. 89-91. https://mendcomm.colab.ws/publications/10.1070/MC1992v002n03ABEH000147.

Abstract

A chiral NiII complex of a Schiff base derived from β-alanine and (S)-2-N(N‘-benzylprolyl)aminobenzophenone (BBP) undergoes an NaH-promoted reaction with benzaldehyde to produce a mixture of two diastereoisomeric complexes which, after chromatographic separation on SiO2 and decomposition with acid, give optically pure (2S,3R)- and (2S,3S)-2-aminomethyl-3-hydroxy-3-phenylpropanoic acids.

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