Chemical Communications, issue 47, pages 7278

Enantioselective iridium-catalyzed carbonyl allylation from the alcohol oxidation level via transfer hydrogenation: minimizing pre-activation for synthetic efficiency

Soo Bong Han ¹

In Su Kim ^{1, 2}

Michael J Krische ¹

Hide authors affiliations Show authors affiliations: 2 affiliations

Department of Chemistry and Biochemistry, University of Texas at Austin, 1 University Station A5300, Austin, USA |

Department of Chemistry, University of Ulsan, Ulsan 680-749, Republic of Korea |

Publication type: Journal Article

Publication date: 2009-10-16

Royal Society of Chemistry (RSC)

Journal: Chemical Communications

Quartile SCImago

Quartile WOS

Impact factor: 4.9

ISSN: 13597345, 1364548X

DOI: 10.1039/b917243m

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Materials Chemistry

Metals and Alloys

Surfaces, Coatings and Films

General Chemistry

Ceramics and Composites

Electronic, Optical and Magnetic Materials

Catalysis

Abstract

Existing methods for enantioselective carbonyl allylation, crotylation and tert-prenylation require stoichiometric generation of pre-metallated nucleophiles, and often employ stoichiometric chiral modifiers. Under the conditions of transfer hydrogenation employing an ortho-cyclometallated iridium C,O-benzoate catalyst, enantioselective carbonyl allylations, crotylations and tert-prenylations are achieved in the absence of stoichiometric metallic reagents or stoichiometric chiral modifiers. Moreover, under transfer hydrogenation conditions, primary alcohols function dually as hydrogen donors and aldehyde precursors, enabling enantioselective carbonyl addition directly from the alcohol oxidation level.

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Chinese Journal of Organic Chemistry	Chinese Journal of Organic Chemistry, 1, 0.88% Chinese Journal of Organic Chemistry 1 publication, 0.88%
Scientific Reports	Scientific Reports, 1, 0.88% Scientific Reports 1 publication, 0.88%
Nature Chemistry	Nature Chemistry, 1, 0.88% Nature Chemistry 1 publication, 0.88%
Inorganica Chimica Acta	Inorganica Chimica Acta, 1, 0.88% Inorganica Chimica Acta 1 publication, 0.88%
Applied Organometallic Chemistry	Applied Organometallic Chemistry, 1, 0.88% Applied Organometallic Chemistry 1 publication, 0.88%
ChemInform	ChemInform, 1, 0.88% ChemInform 1 publication, 0.88%
ChemCatChem	ChemCatChem, 1, 0.88% ChemCatChem 1 publication, 0.88%
Energy and Environmental Science	Energy and Environmental Science, 1, 0.88% Energy and Environmental Science 1 publication, 0.88%
RSC Advances	RSC Advances, 1, 0.88% RSC Advances 1 publication, 0.88%
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	2 4 6 8 10 12 14

Citations by publishers

	5 10 15 20 25 30 35 40 45
Wiley	Wiley, 45, 39.82% Wiley 45 publications, 39.82%
American Chemical Society (ACS)	American Chemical Society (ACS), 36, 31.86% American Chemical Society (ACS) 36 publications, 31.86%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 16, 14.16% Royal Society of Chemistry (RSC) 16 publications, 14.16%
Elsevier	Elsevier, 9, 7.96% Elsevier 9 publications, 7.96%
Springer Nature	Springer Nature, 4, 3.54% Springer Nature 4 publications, 3.54%
The Chemical Society of Japan	The Chemical Society of Japan, 1, 0.88% The Chemical Society of Japan 1 publication, 0.88%
Shanghai Institute of Organic Chemistry	Shanghai Institute of Organic Chemistry, 1, 0.88% Shanghai Institute of Organic Chemistry 1 publication, 0.88%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 0.88% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 0.88%
	5 10 15 20 25 30 35 40 45

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Han S. B. et al. Enantioselective iridium-catalyzed carbonyl allylation from the alcohol oxidation level via transfer hydrogenation: minimizing pre-activation for synthetic efficiency // Chemical Communications. 2009. Vol. 47. p. 7278.

GOST all authors (up to 50) Copy

Han S. B., Kim I. S., Krische M. J. Enantioselective iridium-catalyzed carbonyl allylation from the alcohol oxidation level via transfer hydrogenation: minimizing pre-activation for synthetic efficiency // Chemical Communications. 2009. Vol. 47. p. 7278.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1039/b917243m

UR - https://doi.org/10.1039/b917243m

TI - Enantioselective iridium-catalyzed carbonyl allylation from the alcohol oxidation level via transfer hydrogenation: minimizing pre-activation for synthetic efficiency

T2 - Chemical Communications

AU - Han, Soo Bong

AU - Kim, In Su

AU - Krische, Michael J

PY - 2009

DA - 2009/10/16 00:00:00

PB - Royal Society of Chemistry (RSC)

SP - 7278

IS - 47

SN - 1359-7345

SN - 1364-548X

ER -

BibTex

Cite this

BibTex Copy

@article{2009_Han,

author = {Soo Bong Han and In Su Kim and Michael J Krische},

title = {Enantioselective iridium-catalyzed carbonyl allylation from the alcohol oxidation level via transfer hydrogenation: minimizing pre-activation for synthetic efficiency},

journal = {Chemical Communications},

year = {2009},

publisher = {Royal Society of Chemistry (RSC)},

month = {oct},

url = {https://doi.org/10.1039/b917243m},

number = {47},

pages = {7278},

doi = {10.1039/b917243m}

}

Found error?

Publisher

Royal Society of Chemistry (RSC)

Journal

Chemical Communications

Quartile SCImago

Quartile WOS

Impact factor

4.9

ISSN

13597345 (Print)
1364548X (Electronic)

Profiles

Kim, In Su