Chiral-Anion-Dependent Inversion of Diastereo- and Enantioselectivity in Carbonyl Crotylation via Ruthenium-Catalyzed Butadiene Hydrohydroxyalkylation
Publication type: Journal Article
Publication date: 2012-12-12
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
23234459
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
The ruthenium catalyst generated in situ from H(2)Ru(CO)(PPh(3))(3), (S)-SEGPHOS, and a TADDOL-derived phosphoric acid promotes butadiene hydrohydroxyalkylation to form enantiomerically enriched products. Notably, the observed diastereo- and enantioselectivity is the opposite of that observed using BINOL-derived phosphate counterions in combination with (S)-SEGPHOS, the same enantiomer of the chiral ligand. Match/mismatch effects between the chiral ligand and the chiral TADDOL-phosphate counterion are described. For the first time, single-crystal X-ray diffraction data for a ruthenium complex modified by a chiral phosphate counterion are reported.
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202
Total citations:
202
Citations from 2024:
19
(9%)
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GOST
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Mcinturff E. L., YAMAGUCHI E., Krische M. J. Chiral-Anion-Dependent Inversion of Diastereo- and Enantioselectivity in Carbonyl Crotylation via Ruthenium-Catalyzed Butadiene Hydrohydroxyalkylation // Journal of the American Chemical Society. 2012. Vol. 134. No. 51. pp. 20628-20631.
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Mcinturff E. L., YAMAGUCHI E., Krische M. J. Chiral-Anion-Dependent Inversion of Diastereo- and Enantioselectivity in Carbonyl Crotylation via Ruthenium-Catalyzed Butadiene Hydrohydroxyalkylation // Journal of the American Chemical Society. 2012. Vol. 134. No. 51. pp. 20628-20631.
Cite this
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TY - JOUR
DO - 10.1021/ja311208a
UR - https://doi.org/10.1021/ja311208a
TI - Chiral-Anion-Dependent Inversion of Diastereo- and Enantioselectivity in Carbonyl Crotylation via Ruthenium-Catalyzed Butadiene Hydrohydroxyalkylation
T2 - Journal of the American Chemical Society
AU - Mcinturff, Emma L
AU - YAMAGUCHI, Eiji
AU - Krische, Michael J
PY - 2012
DA - 2012/12/12
PB - American Chemical Society (ACS)
SP - 20628-20631
IS - 51
VL - 134
PMID - 23234459
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
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@article{2012_Mcinturff,
author = {Emma L Mcinturff and Eiji YAMAGUCHI and Michael J Krische},
title = {Chiral-Anion-Dependent Inversion of Diastereo- and Enantioselectivity in Carbonyl Crotylation via Ruthenium-Catalyzed Butadiene Hydrohydroxyalkylation},
journal = {Journal of the American Chemical Society},
year = {2012},
volume = {134},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/ja311208a},
number = {51},
pages = {20628--20631},
doi = {10.1021/ja311208a}
}
Cite this
MLA
Copy
Mcinturff, Emma L., et al. “Chiral-Anion-Dependent Inversion of Diastereo- and Enantioselectivity in Carbonyl Crotylation via Ruthenium-Catalyzed Butadiene Hydrohydroxyalkylation.” Journal of the American Chemical Society, vol. 134, no. 51, Dec. 2012, pp. 20628-20631. https://doi.org/10.1021/ja311208a.