Enantioselective Synthesis of Both Enantiomers of Methyl Dihydrojasmonate Using Solid−Liquid Asymmetric Phase-Transfer Catalysis
1
Laboratoire des Fonctions Azotées et Oxygénées Complexes - IRCOF, UPRES-A CNRS 6014, Faculté des Sciences, rue Tesnière, F-76821 Mont Saint Aignan Cedex, France, and Rhodia Organique Fine, Centre de Recherche de Lyon, 85, avenue des Frères Perret, BP 62, F-69192 Saint Fons Cedex, France
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Publication type: Journal Article
Publication date: 2000-08-31
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
10986082
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Both enantiomers of methyl dihydrojasmonate (−)-1 and (+)-1 were obtained by a short route using asymmetric Michael addition of dimethyl malonate onto pentyl enone 3, followed by nonracemizing demethoxycarbonylation. The key enantioselective step involves a new system of asymmetric solid−liquid phase-transfer catalysis using solvent-free conditions. Enantiomeric excess as high as 90% (91% yield) was achieved.
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Total citations:
85
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GOST
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Perrard T. et al. Enantioselective Synthesis of Both Enantiomers of Methyl Dihydrojasmonate Using Solid−Liquid Asymmetric Phase-Transfer Catalysis // Organic Letters. 2000. Vol. 2. No. 19. pp. 2959-2962.
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Perrard T., Plaquevent J., Desmurs J., Hebrault D. Enantioselective Synthesis of Both Enantiomers of Methyl Dihydrojasmonate Using Solid−Liquid Asymmetric Phase-Transfer Catalysis // Organic Letters. 2000. Vol. 2. No. 19. pp. 2959-2962.
Cite this
RIS
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TY - JOUR
DO - 10.1021/ol006207e
UR - https://doi.org/10.1021/ol006207e
TI - Enantioselective Synthesis of Both Enantiomers of Methyl Dihydrojasmonate Using Solid−Liquid Asymmetric Phase-Transfer Catalysis
T2 - Organic Letters
AU - Perrard, Thierry
AU - Plaquevent, Jean-Christophe
AU - Desmurs, Jean-Roger
AU - Hebrault, Dominique
PY - 2000
DA - 2000/08/31
PB - American Chemical Society (ACS)
SP - 2959-2962
IS - 19
VL - 2
PMID - 10986082
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2000_Perrard,
author = {Thierry Perrard and Jean-Christophe Plaquevent and Jean-Roger Desmurs and Dominique Hebrault},
title = {Enantioselective Synthesis of Both Enantiomers of Methyl Dihydrojasmonate Using Solid−Liquid Asymmetric Phase-Transfer Catalysis},
journal = {Organic Letters},
year = {2000},
volume = {2},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/ol006207e},
number = {19},
pages = {2959--2962},
doi = {10.1021/ol006207e}
}
Cite this
MLA
Copy
Perrard, Thierry, et al. “Enantioselective Synthesis of Both Enantiomers of Methyl Dihydrojasmonate Using Solid−Liquid Asymmetric Phase-Transfer Catalysis.” Organic Letters, vol. 2, no. 19, Aug. 2000, pp. 2959-2962. https://doi.org/10.1021/ol006207e.