An Efficient Protocol for the Enantioselective Preparation of a Key Polyfunctionalized Cyclohexane. New Access to (R)- and (S)-4-Hydroxy-2-cyclohexenone and (R)- and (S)-trans-Cyclohex-2-ene-1,4-diol
Тип публикации: Journal Article
Дата публикации: 2008-03-26
scimago Q2
wos Q1
БС1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
18363375
Organic Chemistry
Краткое описание
Starting from very accessible raw materials such as p-methoxyphenol, ethylene glycol, and thiophenol, a protocol has been developed to prepare multigram quantities of the polyfunctionalized cyclohexane (+/-)- 7. A highly efficient resolution of (+/-)- 7 has been achieved through enantioselective acetylation catalyzed by Candida antarctica lipase B. Straightforward and enantioselective syntheses of 4-hydroxy-2-cyclohexenone, 1, trans-cyclohex-2-ene-1,4-diol, 2, and their O-protected derivatives 18 and 19 have been readily accomplished from 7.
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19
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Bayón P. et al. An Efficient Protocol for the Enantioselective Preparation of a Key Polyfunctionalized Cyclohexane. New Access to (R)- and (S)-4-Hydroxy-2-cyclohexenone and (R)- and (S)-trans-Cyclohex-2-ene-1,4-diol // Journal of Organic Chemistry. 2008. Vol. 73. No. 9. pp. 3486-3491.
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Bayón P., Marjanet G., Toribio G., Alibés R., de March P., Figueredo M., FONT J. An Efficient Protocol for the Enantioselective Preparation of a Key Polyfunctionalized Cyclohexane. New Access to (R)- and (S)-4-Hydroxy-2-cyclohexenone and (R)- and (S)-trans-Cyclohex-2-ene-1,4-diol // Journal of Organic Chemistry. 2008. Vol. 73. No. 9. pp. 3486-3491.
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TY - JOUR
DO - 10.1021/jo800107h
UR - https://doi.org/10.1021/jo800107h
TI - An Efficient Protocol for the Enantioselective Preparation of a Key Polyfunctionalized Cyclohexane. New Access to (R)- and (S)-4-Hydroxy-2-cyclohexenone and (R)- and (S)-trans-Cyclohex-2-ene-1,4-diol
T2 - Journal of Organic Chemistry
AU - Bayón, Pau
AU - Marjanet, Georgina
AU - Toribio, Gladis
AU - Alibés, Ramon
AU - de March, Pere
AU - Figueredo, Marta
AU - FONT, JOSEP
PY - 2008
DA - 2008/03/26
PB - American Chemical Society (ACS)
SP - 3486-3491
IS - 9
VL - 73
PMID - 18363375
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2008_Bayón,
author = {Pau Bayón and Georgina Marjanet and Gladis Toribio and Ramon Alibés and Pere de March and Marta Figueredo and JOSEP FONT},
title = {An Efficient Protocol for the Enantioselective Preparation of a Key Polyfunctionalized Cyclohexane. New Access to (R)- and (S)-4-Hydroxy-2-cyclohexenone and (R)- and (S)-trans-Cyclohex-2-ene-1,4-diol},
journal = {Journal of Organic Chemistry},
year = {2008},
volume = {73},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/jo800107h},
number = {9},
pages = {3486--3491},
doi = {10.1021/jo800107h}
}
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MLA
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Bayón, Pau, et al. “An Efficient Protocol for the Enantioselective Preparation of a Key Polyfunctionalized Cyclohexane. New Access to (R)- and (S)-4-Hydroxy-2-cyclohexenone and (R)- and (S)-trans-Cyclohex-2-ene-1,4-diol.” Journal of Organic Chemistry, vol. 73, no. 9, Mar. 2008, pp. 3486-3491. https://doi.org/10.1021/jo800107h.