Home / Publications / Efficient synthesis of β-hydroxy sulfides by microwave-promoted ring opening in (+)-3-carene trans-epoxide with sodium thiolates

Efficient synthesis of β-hydroxy sulfides by microwave-promoted ring opening in (+)-3-carene trans-epoxide with sodium thiolates

Alexander Mikhailovich Agafontsev 1
Alexander Mikhailovich Agafontsev
, 
Nikolaj Borisovich Gorshkov 1
Nikolaj Borisovich Gorshkov
, 
Alexey Vasil'evich Tkachev 1, 2
Alexey Vasil'evich Tkachev
10.1016/j.mencom.2011.07.006
Published 2011-07-01
Communication , Volume 21, Issue 4, 192-193
4
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Agafontsev A. M., Gorshkov N. B., Tkachev A. V. Efficient synthesis of β-hydroxy sulfides by microwave-promoted ring opening in (+)-3-carene trans-epoxide with sodium thiolates // Mendeleev Communications. 2011. Vol. 21. No. 4. pp. 192-193.
GOST all authors (up to 50) Copy
Agafontsev A. M., Gorshkov N. B., Tkachev A. V. Efficient synthesis of β-hydroxy sulfides by microwave-promoted ring opening in (+)-3-carene trans-epoxide with sodium thiolates // Mendeleev Communications. 2011. Vol. 21. No. 4. pp. 192-193.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2011.07.006
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.07.006
TI - Efficient synthesis of β-hydroxy sulfides by microwave-promoted ring opening in (+)-3-carene trans-epoxide with sodium thiolates
T2 - Mendeleev Communications
AU - Agafontsev, Alexander Mikhailovich
AU - Gorshkov, Nikolaj Borisovich
AU - Tkachev, Alexey Vasil'evich
PY - 2011
DA - 2011/07/01
PB - Mendeleev Communications
SP - 192-193
IS - 4
VL - 21
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2011_Agafontsev,
author = {Alexander Mikhailovich Agafontsev and Nikolaj Borisovich Gorshkov and Alexey Vasil'evich Tkachev},
title = {Efficient synthesis of β-hydroxy sulfides by microwave-promoted ring opening in (+)-3-carene trans-epoxide with sodium thiolates},
journal = {Mendeleev Communications},
year = {2011},
volume = {21},
publisher = {Mendeleev Communications},
month = {Jul},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.07.006},
number = {4},
pages = {192--193},
doi = {10.1016/j.mencom.2011.07.006}
}
MLA
Cite this
MLA Copy
Agafontsev, Alexander Mikhailovich, et al. “Efficient synthesis of β-hydroxy sulfides by microwave-promoted ring opening in (+)-3-carene trans-epoxide with sodium thiolates.” Mendeleev Communications, vol. 21, no. 4, Jul. 2011, pp. 192-193. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.07.006.

Abstract

Reaction of (+)-3-carene trans-epoxide with sodium thiolates in methanolic solution in a microwave oven at 140°C for 35–40min affords corresponding (1S,3S,4S,6R)-4-sulfanylcaran-3-ols in 75–95% yields.

References

2.
Improved procedure for Juliá–Colonna asymmetric epoxidation of α,β-unsaturated ketones: total synthesis of diltiazem and Taxol TM side-chain
Adger B.M., Barkley J.V., Bergeron S., Cappi M.W., Flowerdew B.E., Jackson M.P., McCague R., Nugent T.C., Roberts S.M.
Journal of the Chemical Society Perkin Transactions 1, 1997
6.
R. Krishnamutri, S. Nagy and T. F. Smolka, US Patent 5621153, 1997.
7.
Enantioselective synthesis of calcium channel blockers of the diltiazem group
Schwartz A., Madan P.B., Mohacsi E., O'Brien J.P., Todaro L.J., Coffen D.L.
Journal of Organic Chemistry, 1992
9.
Stereospecific total synthesis of a "slow reacting substance" of anaphylaxis, leukotriene C-1
Corey E.J., Clark D.A., Goto G., Marfat A., Mioskowski C., Samuelsson B., Hammarstroem S.
Journal of the American Chemical Society, 1980
12.
Chiral Sulfur Ligands for Asymmetric Catalysis
Mellah M., Voituriez A., Schulz E.
Chemical Reviews, 2007
15.
10.1016/j.mencom.2011.07.006_bib0040_2
Iqbal
Tetrahedron, 1990
16.
Selective oxidation of sulfides: selective preparation of 1-trifluoromethyl vinyl sulfoxides
Ravikumar K.S., Barbier F., Bégué J., Bonnet-Delpon D.
Journal of Fluorine Chemistry, 1999
17.
Magnesium Chloride–Catalyzed Thiolysis of Epoxides: Synthesis ofβ-hydroxy Sulfides
Rani R., Pattanayak S., Agarwal J., Peddinti R.K.
Synthetic Communications, 2010
19.
10.1016/j.mencom.2011.07.006_bib0050
Yu
Synlett, 2007
22.
10.1016/j.mencom.2011.07.006_bib0060
Kesavan
Tetrahedron Lett., 2000
26.
10.1016/j.mencom.2011.07.006_bib0080
Artemova
Zh. Obshch. Khim., 1989
27.
10.1016/j.mencom.2011.07.006_bib0085
Artemova
Zh. Obshch. Khim., 1990
28.
10.1016/j.mencom.2011.07.006_bib0090
Artemova
Zh. Obshch. Khim., 1991
29.
10.1016/j.mencom.2011.07.006_bib0095
Artemova
Khim. Prir. Soedin., 1991
30.
V. V. Plemenkov, G. Sh. Bikbulatova, N.P. Artemova, L.N. Surkova, A.V. Iliasov and A. A. Nafikova, USSR Inventor's Certificate 1498760, C07C, 1989
31.
Glossary
The Adelphi Papers, 1989