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Efficient and stereoselective synthesis of (S)-α-propargylglycine derivatives from allenylboronic acid

Veronika A Morozova 1
Veronika A Morozova
,  , 
Igor Dem'yanovich Titanyuk 1
Igor Dem'yanovich Titanyuk
10.1016/j.mencom.2019.09.006
Published 2019-09-04
Communication , Volume 29, Issue 5, 498-499
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Morozova V. A., Beletskaya I. P., Titanyuk I. D. Efficient and stereoselective synthesis of (S)-α-propargylglycine derivatives from allenylboronic acid // Mendeleev Communications. 2019. Vol. 29. No. 5. pp. 498-499.
GOST all authors (up to 50) Copy
Morozova V. A., Beletskaya I. P., Titanyuk I. D. Efficient and stereoselective synthesis of (S)-α-propargylglycine derivatives from allenylboronic acid // Mendeleev Communications. 2019. Vol. 29. No. 5. pp. 498-499.
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TY - JOUR
DO - 10.1016/j.mencom.2019.09.006
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.09.006
TI - Efficient and stereoselective synthesis of (S)-α-propargylglycine derivatives from allenylboronic acid
T2 - Mendeleev Communications
AU - Morozova, Veronika A
AU - Beletskaya, Irina Petrovna
AU - Titanyuk, Igor Dem'yanovich
PY - 2019
DA - 2019/09/04
PB - Mendeleev Communications
SP - 498-499
IS - 5
VL - 29
ER -
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@article{2019_Morozova,
author = {Veronika A Morozova and Irina Petrovna Beletskaya and Igor Dem'yanovich Titanyuk},
title = {Efficient and stereoselective synthesis of (S)-α-propargylglycine derivatives from allenylboronic acid},
journal = {Mendeleev Communications},
year = {2019},
volume = {29},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.09.006},
number = {5},
pages = {498--499},
doi = {10.1016/j.mencom.2019.09.006}
}
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Morozova, Veronika A., et al. “Efficient and stereoselective synthesis of (S)-α-propargylglycine derivatives from allenylboronic acid.” Mendeleev Communications, vol. 29, no. 5, Sep. 2019, pp. 498-499. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.09.006.

Abstract

The Petasis–Mannich reaction of allenylboronic acid with glyoxylic acid and (S)-1-phenylethylamine diastereoselectively leads to N-substituted propargylglycine of high optical purity in good yield. This product can be further subjected to esterification followed by bioconjugate synthesis using CuI-catalyzed alkyne–azide 1,3-dipolar cycloaddition reaction (‘click reaction’).

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