Journal of the American Chemical Society, volume 134, issue 51, pages 20628-20631

Chiral-Anion-Dependent Inversion of Diastereo- and Enantioselectivity in Carbonyl Crotylation via Ruthenium-Catalyzed Butadiene Hydrohydroxyalkylation

Emma L Mcinturff ¹

Eiji YAMAGUCHI ¹

Michael J Krische ¹

Hide authors affiliations Show authors affiliations: 1 affiliation

Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, United States |

Publication type: Journal Article

Publication date: 2012-12-12

American Chemical Society (ACS)

Journal: Journal of the American Chemical Society

Quartile SCImago

Quartile WOS

Impact factor: 15

ISSN: 00027863, 15205126

DOI: 10.1021/ja311208a

Copy DOI

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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Journal of the American Chemical Society	Journal of the American Chemical Society, 39, 20.21% Journal of the American Chemical Society 39 publications, 20.21%
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Chemical Reviews	Chemical Reviews, 6, 3.11% Chemical Reviews 6 publications, 3.11%
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 6, 3.11% Advanced Synthesis and Catalysis 6 publications, 3.11%
ACS Catalysis	ACS Catalysis, 6, 3.11% ACS Catalysis 6 publications, 3.11%
Chemical Communications	Chemical Communications, 6, 3.11% Chemical Communications 6 publications, 3.11%
Nature Communications	Nature Communications, 3, 1.55% Nature Communications 3 publications, 1.55%
Journal of Organic Chemistry	Journal of Organic Chemistry, 3, 1.55% Journal of Organic Chemistry 3 publications, 1.55%
Synlett	Synlett, 2, 1.04% Synlett 2 publications, 1.04%
Tetrahedron	Tetrahedron, 2, 1.04% Tetrahedron 2 publications, 1.04%
Accounts of Chemical Research	Accounts of Chemical Research, 2, 1.04% Accounts of Chemical Research 2 publications, 1.04%
RSC Advances	RSC Advances, 2, 1.04% RSC Advances 2 publications, 1.04%
Science	Science, 2, 1.04% Science 2 publications, 1.04%
Synthesis	Synthesis, 2, 1.04% Synthesis 2 publications, 1.04%
Acta crystallographica. Section C, Structural chemistry	Acta crystallographica. Section C, Structural chemistry, 1, 0.52% Acta crystallographica. Section C, Structural chemistry 1 publication, 0.52%
Chinese Journal of Organic Chemistry	Chinese Journal of Organic Chemistry, 1, 0.52% Chinese Journal of Organic Chemistry 1 publication, 0.52%
Nature	Nature, 1, 0.52% Nature 1 publication, 0.52%
Topics in Current Chemistry	Topics in Current Chemistry, 1, 0.52% Topics in Current Chemistry 1 publication, 0.52%
Trends in Chemistry	Trends in Chemistry, 1, 0.52% Trends in Chemistry 1 publication, 0.52%
Coordination Chemistry Reviews	Coordination Chemistry Reviews, 1, 0.52% Coordination Chemistry Reviews 1 publication, 0.52%
Current Opinion in Green and Sustainable Chemistry	Current Opinion in Green and Sustainable Chemistry, 1, 0.52% Current Opinion in Green and Sustainable Chemistry 1 publication, 0.52%
Tetrahedron Letters	Tetrahedron Letters, 1, 0.52% Tetrahedron Letters 1 publication, 0.52%
ChemCatChem	ChemCatChem, 1, 0.52% ChemCatChem 1 publication, 0.52%
Chirality	Chirality, 1, 0.52% Chirality 1 publication, 0.52%
Israel Journal of Chemistry	Israel Journal of Chemistry, 1, 0.52% Israel Journal of Chemistry 1 publication, 0.52%
	5 10 15 20 25 30 35 40

Citations by publishers

	10 20 30 40 50 60 70 80
Wiley	Wiley, 77, 39.9% Wiley 77 publications, 39.9%
American Chemical Society (ACS)	American Chemical Society (ACS), 72, 37.31% American Chemical Society (ACS) 72 publications, 37.31%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 21, 10.88% Royal Society of Chemistry (RSC) 21 publications, 10.88%
Elsevier	Elsevier, 6, 3.11% Elsevier 6 publications, 3.11%
Springer Nature	Springer Nature, 5, 2.59% Springer Nature 5 publications, 2.59%
Thieme	Thieme, 4, 2.07% Thieme 4 publications, 2.07%
American Association for the Advancement of Science (AAAS)	American Association for the Advancement of Science (AAAS), 2, 1.04% American Association for the Advancement of Science (AAAS) 2 publications, 1.04%
International Union of Crystallography (IUCr)	International Union of Crystallography (IUCr), 1, 0.52% International Union of Crystallography (IUCr) 1 publication, 0.52%
Shanghai Institute of Organic Chemistry	Shanghai Institute of Organic Chemistry, 1, 0.52% Shanghai Institute of Organic Chemistry 1 publication, 0.52%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 0.52% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 0.52%
	10 20 30 40 50 60 70 80

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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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RIS |

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RIS Copy

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 00:00:00

PB - American Chemical Society (ACS)

SP - 20628-20631

IS - 51

VL - 134

PMID - 23234459

SN - 0002-7863

SN - 1520-5126

ER -

BibTex |

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BibTex Copy

@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}

}

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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.

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Publisher

American Chemical Society (ACS)

Journal

Journal of the American Chemical Society

Quartile SCImago

Quartile WOS

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ISSN

00027863 (Print)
15205126 (Electronic)