Efficient Enantioselective Synthesis of Functionalized Tetrahydropyrans by Ru-Catalyzed Asymmetric Ring-Opening Metathesis/Cross-Metathesis (AROM/CM)
Publication type: Journal Article
Publication date: 2004-09-14
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
15453761
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
An efficient method for enantioselective synthesis of highly functionalized pyrans (up to 98% ee) through Ru-catalyzed asymmetric ring-opening metathesis/cross-metathesis is described. Reactions are promoted by a recyclable chiral Ru-chloride or a new chiral Ru-iodide complex; the latter catalyst is less efficient but gives rise to significantly higher levels of enantioselectivity. Catalytic reactions can be performed in undistilled solvent and with a wide range of substrates, including those that contain secondary and tertiary alcohols. Representative regioselective functionalizations that highlight the utility of the catalytic method are also presented.
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Metrics
139
Total citations:
139
Citations from 2024:
2
(1.44%)
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GOST
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Gillingham D. et al. Efficient Enantioselective Synthesis of Functionalized Tetrahydropyrans by Ru-Catalyzed Asymmetric Ring-Opening Metathesis/Cross-Metathesis (AROM/CM) // Journal of the American Chemical Society. 2004. Vol. 126. No. 39. pp. 12288-12290.
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Gillingham D., KATAOKA O., Garber S. B., Hoveyda A. H. Efficient Enantioselective Synthesis of Functionalized Tetrahydropyrans by Ru-Catalyzed Asymmetric Ring-Opening Metathesis/Cross-Metathesis (AROM/CM) // Journal of the American Chemical Society. 2004. Vol. 126. No. 39. pp. 12288-12290.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/ja0458672
UR - https://doi.org/10.1021/ja0458672
TI - Efficient Enantioselective Synthesis of Functionalized Tetrahydropyrans by Ru-Catalyzed Asymmetric Ring-Opening Metathesis/Cross-Metathesis (AROM/CM)
T2 - Journal of the American Chemical Society
AU - Gillingham, Dennis
AU - KATAOKA, Osamu
AU - Garber, Steven B
AU - Hoveyda, Amir H.
PY - 2004
DA - 2004/09/14
PB - American Chemical Society (ACS)
SP - 12288-12290
IS - 39
VL - 126
PMID - 15453761
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
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@article{2004_Gillingham,
author = {Dennis Gillingham and Osamu KATAOKA and Steven B Garber and Amir H. Hoveyda},
title = {Efficient Enantioselective Synthesis of Functionalized Tetrahydropyrans by Ru-Catalyzed Asymmetric Ring-Opening Metathesis/Cross-Metathesis (AROM/CM)},
journal = {Journal of the American Chemical Society},
year = {2004},
volume = {126},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/ja0458672},
number = {39},
pages = {12288--12290},
doi = {10.1021/ja0458672}
}
Cite this
MLA
Copy
Gillingham, Dennis, et al. “Efficient Enantioselective Synthesis of Functionalized Tetrahydropyrans by Ru-Catalyzed Asymmetric Ring-Opening Metathesis/Cross-Metathesis (AROM/CM).” Journal of the American Chemical Society, vol. 126, no. 39, Sep. 2004, pp. 12288-12290. https://doi.org/10.1021/ja0458672.