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A novel diastereoselective α-functionalization of proline with benzaldehydes: synthesis of α-(α-hydroxybenzyl)prolines

Alexander Victorovich Pavlushin 1
Alexander Victorovich Pavlushin
,  , 
Vyacheslav Yakovlevich Sosnovskikh 1
Vyacheslav Yakovlevich Sosnovskikh
10.1016/j.mencom.2017.11.031
Published 2017-10-30
Communication , Volume 27, Issue 6, 628-630
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Pavlushin A. V., Moshkin V. S., Sosnovskikh V. Y. A novel diastereoselective α-functionalization of proline with benzaldehydes: synthesis of α-(α-hydroxybenzyl)prolines // Mendeleev Communications. 2017. Vol. 27. No. 6. pp. 628-630.
GOST all authors (up to 50) Copy
Pavlushin A. V., Moshkin V. S., Sosnovskikh V. Y. A novel diastereoselective α-functionalization of proline with benzaldehydes: synthesis of α-(α-hydroxybenzyl)prolines // Mendeleev Communications. 2017. Vol. 27. No. 6. pp. 628-630.
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TY - JOUR
DO - 10.1016/j.mencom.2017.11.031
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.11.031
TI - A novel diastereoselective α-functionalization of proline with benzaldehydes: synthesis of α-(α-hydroxybenzyl)prolines
T2 - Mendeleev Communications
AU - Pavlushin, Alexander Victorovich
AU - Moshkin, Vladimir Sergeevich
AU - Sosnovskikh, Vyacheslav Yakovlevich
PY - 2017
DA - 2017/10/30
PB - Mendeleev Communications
SP - 628-630
IS - 6
VL - 27
ER -
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@article{2017_Pavlushin,
author = {Alexander Victorovich Pavlushin and Vladimir Sergeevich Moshkin and Vyacheslav Yakovlevich Sosnovskikh},
title = {A novel diastereoselective α-functionalization of proline with benzaldehydes: synthesis of α-(α-hydroxybenzyl)prolines},
journal = {Mendeleev Communications},
year = {2017},
volume = {27},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.11.031},
number = {6},
pages = {628--630},
doi = {10.1016/j.mencom.2017.11.031}
}
MLA
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Pavlushin, Alexander Victorovich, et al. “A novel diastereoselective α-functionalization of proline with benzaldehydes: synthesis of α-(α-hydroxybenzyl)prolines.” Mendeleev Communications, vol. 27, no. 6, Oct. 2017, pp. 628-630. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.11.031.

Abstract

2-Oxapyrrolizidines formed in reactions of methyl prolinate with two molecules of aromatic aldehyde upon gradual hydrolysis give α-(α-hydroxybenzyl)prolines. The products are preferentially formed as one diastereomer (91–100%) in overall yield 33–50% (five stages starting from proline).

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