A practical enantioselective synthesis of (S)-3-hydroxytetradecanoic acid
1
The 1st Laboratories, Research and Development Center, Nagase & Co., Ltd, 2-2-3 Murotani, Nishi-ku, Kobe 651-2241, Japan
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Publication type: Journal Article
Publication date: 1999-07-01
Catalysis
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
(S)-3-Hydroxytetradecanoic acid 1 has been synthesized in an overall yield of 27% from (S)-epichlorohydrin 2 as follows: (1) regio and chemoselective epoxide opening of 2 with a Grignard reagent under the catalysis by Cu(I) followed by consecutive epoxide formation; (2) regioselective epoxide opening of (S)-1,2-epoxytridecane 4 with cyanide anion under pH controlled conditions followed by consecutive nitrile hydrolysis with alkaline H2O2 gave crude 1; (3) its purification via the N,N-dicyclohexylammonium salt 6. The method thus devised is practical and scalable for the industrial production of 1.
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MATSUYAMA K., Ikunaka M. A practical enantioselective synthesis of (S)-3-hydroxytetradecanoic acid // Tetrahedron Asymmetry. 1999. Vol. 10. No. 15. pp. 2945-2950.
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MATSUYAMA K., Ikunaka M. A practical enantioselective synthesis of (S)-3-hydroxytetradecanoic acid // Tetrahedron Asymmetry. 1999. Vol. 10. No. 15. pp. 2945-2950.
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TY - JOUR
DO - 10.1016/s0957-4166(99)00290-6
UR - https://doi.org/10.1016/s0957-4166(99)00290-6
TI - A practical enantioselective synthesis of (S)-3-hydroxytetradecanoic acid
T2 - Tetrahedron Asymmetry
AU - MATSUYAMA, Keisuke
AU - Ikunaka, Masaya
PY - 1999
DA - 1999/07/01
PB - Elsevier
SP - 2945-2950
IS - 15
VL - 10
SN - 0957-4166
SN - 1362-511X
ER -
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BibTex (up to 50 authors)
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@article{1999_MATSUYAMA,
author = {Keisuke MATSUYAMA and Masaya Ikunaka},
title = {A practical enantioselective synthesis of (S)-3-hydroxytetradecanoic acid},
journal = {Tetrahedron Asymmetry},
year = {1999},
volume = {10},
publisher = {Elsevier},
month = {jul},
url = {https://doi.org/10.1016/s0957-4166(99)00290-6},
number = {15},
pages = {2945--2950},
doi = {10.1016/s0957-4166(99)00290-6}
}
Cite this
MLA
Copy
MATSUYAMA, Keisuke, and Masaya Ikunaka. “A practical enantioselective synthesis of (S)-3-hydroxytetradecanoic acid.” Tetrahedron Asymmetry, vol. 10, no. 15, Jul. 1999, pp. 2945-2950. https://doi.org/10.1016/s0957-4166(99)00290-6.