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Enantiopure vicinally trisubstituted all-cis-bis(hydroxymethyl)-cyclopentenols and their derivatives

Airat Maratovich Gimazetdinov 1
Airat Maratovich Gimazetdinov
, 
Aidar Zufarovich Al'mukhametov 1
Aidar Zufarovich Al'mukhametov
, 
Vladimir Valer'evich Loza 1
Vladimir Valer'evich Loza
, 
Leonid Vasilevich Spirikhin 1
Leonid Vasilevich Spirikhin
, 
Mansur Sagar'yarovich Miftakhov 1
Mansur Sagar'yarovich Miftakhov
10.1016/j.mencom.2018.09.033
Published 2018-09-07
Communication , Volume 28, Issue 5, 546-547
6
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Gimazetdinov A. M. et al. Enantiopure vicinally trisubstituted all-cis-bis(hydroxymethyl)-cyclopentenols and their derivatives // Mendeleev Communications. 2018. Vol. 28. No. 5. pp. 546-547.
GOST all authors (up to 50) Copy
Gimazetdinov A. M., Al'mukhametov A. Z., Loza V. V., Spirikhin L. V., Miftakhov M. S. Enantiopure vicinally trisubstituted all-cis-bis(hydroxymethyl)-cyclopentenols and their derivatives // Mendeleev Communications. 2018. Vol. 28. No. 5. pp. 546-547.
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TY - JOUR
DO - 10.1016/j.mencom.2018.09.033
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.09.033
TI - Enantiopure vicinally trisubstituted all-cis-bis(hydroxymethyl)-cyclopentenols and their derivatives
T2 - Mendeleev Communications
AU - Gimazetdinov, Airat Maratovich
AU - Al'mukhametov, Aidar Zufarovich
AU - Loza, Vladimir Valer'evich
AU - Spirikhin, Leonid Vasilevich
AU - Miftakhov, Mansur Sagar'yarovich
PY - 2018
DA - 2018/09/07
PB - Mendeleev Communications
SP - 546-547
IS - 5
VL - 28
ER -
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@article{2018_Gimazetdinov,
author = {Airat Maratovich Gimazetdinov and Aidar Zufarovich Al'mukhametov and Vladimir Valer'evich Loza and Leonid Vasilevich Spirikhin and Mansur Sagar'yarovich Miftakhov},
title = {Enantiopure vicinally trisubstituted all-cis-bis(hydroxymethyl)-cyclopentenols and their derivatives},
journal = {Mendeleev Communications},
year = {2018},
volume = {28},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.09.033},
number = {5},
pages = {546--547},
doi = {10.1016/j.mencom.2018.09.033}
}
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Gimazetdinov, Airat Maratovich, et al. “Enantiopure vicinally trisubstituted all-cis-bis(hydroxymethyl)-cyclopentenols and their derivatives.” Mendeleev Communications, vol. 28, no. 5, Sep. 2018, pp. 546-547. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.09.033.

Abstract

Oxidations of {(1R,4R,5S)-2-[tert-butyl(dimethyl)silyloxy-methyl]-4-(trimethylsilyl)cyclopent-2-en-1-yl}methanol with m-chloroperoxybenzoic acid (mCPBA) and dimethyldioxirane were studied. In the case of mCPBA, an allylicic alcohol expected according to the protodesilylation mechanism and an anomalous product of 1,2-migration of the Me3Si group were obtained. The latter was formed due to the coordination and directing effects of the free OH group.

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