Synthesis and Application of Chiral Cyclopropane-Based Ligands in Palladium-Catalyzed Allylic Alkylation
Publication type: Journal Article
Publication date: 2004-10-19
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
15527291
Organic Chemistry
Abstract
A series of chiral, cyclopropane-based phosphorus/sulfur ligands have been synthesized and evaluated in the palladium-catalyzed allylic alkylation of 1,3-diphenylpropenyl acetate with dimethyl malonate. Variation of the ligand substituents at phosphorus, sulfur, and the carbon backbone revealed 24d to have the optimal configuration for this reaction, giving the product in high yield and with good enantioselectivity (93%). A model for the observed enantioselectivity is discussed within the context of existing models, using X-ray crystallographic data, solution-phase NMR studies, and the absolute stereochemistry of the products. Selected ligands were also evaluated in the palladium-catalyzed intermolecular Heck reaction and the rhodium-catalyzed hydrogenation of a dehydroamino acid.
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Total citations:
74
Citations from 2025:
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(1.35%)
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GOST
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Molander G. A., Burke J. P., Carroll P. Synthesis and Application of Chiral Cyclopropane-Based Ligands in Palladium-Catalyzed Allylic Alkylation // Journal of Organic Chemistry. 2004. Vol. 69. No. 23. pp. 8062-8069.
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Molander G. A., Burke J. P., Carroll P. Synthesis and Application of Chiral Cyclopropane-Based Ligands in Palladium-Catalyzed Allylic Alkylation // Journal of Organic Chemistry. 2004. Vol. 69. No. 23. pp. 8062-8069.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jo048782s
UR - https://doi.org/10.1021/jo048782s
TI - Synthesis and Application of Chiral Cyclopropane-Based Ligands in Palladium-Catalyzed Allylic Alkylation
T2 - Journal of Organic Chemistry
AU - Molander, Gary A.
AU - Burke, Jason P
AU - Carroll, Patrick
PY - 2004
DA - 2004/10/19
PB - American Chemical Society (ACS)
SP - 8062-8069
IS - 23
VL - 69
PMID - 15527291
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2004_Molander,
author = {Gary A. Molander and Jason P Burke and Patrick Carroll},
title = {Synthesis and Application of Chiral Cyclopropane-Based Ligands in Palladium-Catalyzed Allylic Alkylation},
journal = {Journal of Organic Chemistry},
year = {2004},
volume = {69},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/jo048782s},
number = {23},
pages = {8062--8069},
doi = {10.1021/jo048782s}
}
Cite this
MLA
Copy
Molander, Gary A., et al. “Synthesis and Application of Chiral Cyclopropane-Based Ligands in Palladium-Catalyzed Allylic Alkylation.” Journal of Organic Chemistry, vol. 69, no. 23, Oct. 2004, pp. 8062-8069. https://doi.org/10.1021/jo048782s.