Angewandte Chemie - International Edition, volume 50, issue 18, pages 4173-4175

Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (α-Trifluoromethyl)allylation from the Alcohol or Aldehyde Oxidation Level

Xin Gao ¹

Yong Jian Zhang ²

Michael J Krische ³

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University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station – A5300, Austin, TX 78712‐1167 (USA) |

University Of Texas At Austin |

University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station – A5300, Austin, TX 78712‐1167, USA, Fax: (+1) 512‐471‐8696 |

Publication type: Journal Article

Publication date: 2011-04-06

Wiley

Journal: Angewandte Chemie - International Edition

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Impact factor: 16.6

ISSN: 14337851, 15213773

DOI: 10.1002/anie.201008296

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General Chemistry

Catalysis

Abstract

Using the ortho-cyclometalated π-allyl iridium precatalyst (R)-I derived from [Ir(cod)Cl]2, 4-cyano-3-nitrobenzoic acid, (R)-SEGPHOS, and allyl acetate, enantioselective transfer hydrogenation of α-(trimethylsilyl)allyl acetate in the presence of aldehydes 2a−i mediated by 2-propanol delivers products of (trimethylsilyl)allylation 4a−i in good isolated yields and with exceptional levels of anti-diastereoselectivity and enantioselectivity (90−99% ee). In the absence of 2-propanol, but under otherwise identical reaction conditions, carbonyl (trimethylsilyl)allylation is achieved directly from the alcohol oxidation level to furnish an equivalent set of adducts 4a−i with roughly equivalent isolated yields and stereoselectivities. To evaluate the synthetic utility of the reaction products 4a−i, adduct 4g was converted to the 1,4-ene-diol 5g via dioxirane-mediated oxidative desilylation with allylic transposition, the allylic alcohol 6g via protodesilylation with allylic transposition, and the γ-lactam 7g via c...

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	1 2 3 4 5
Journal of the American Chemical Society	Journal of the American Chemical Society, 5, 10.64% Journal of the American Chemical Society 5 publications, 10.64%
Organic Letters	Organic Letters, 4, 8.51% Organic Letters 4 publications, 8.51%
Angewandte Chemie - International Edition	Angewandte Chemie - International Edition, 3, 6.38% Angewandte Chemie - International Edition 3 publications, 6.38%
Angewandte Chemie	Angewandte Chemie, 3, 6.38% Angewandte Chemie 3 publications, 6.38%
Chemistry - A European Journal	Chemistry - A European Journal, 3, 6.38% Chemistry - A European Journal 3 publications, 6.38%
Chemical Communications	Chemical Communications, 3, 6.38% Chemical Communications 3 publications, 6.38%
Organic Process Research and Development	Organic Process Research and Development, 2, 4.26% Organic Process Research and Development 2 publications, 4.26%
ACS Catalysis	ACS Catalysis, 2, 4.26% ACS Catalysis 2 publications, 4.26%
Journal of Organic Chemistry	Journal of Organic Chemistry, 2, 4.26% Journal of Organic Chemistry 2 publications, 4.26%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 2, 4.26% Organic and Biomolecular Chemistry 2 publications, 4.26%
Chemical Science	Chemical Science, 2, 4.26% Chemical Science 2 publications, 4.26%
Chinese Journal of Organic Chemistry	Chinese Journal of Organic Chemistry, 1, 2.13% Chinese Journal of Organic Chemistry 1 publication, 2.13%
Scientific Reports	Scientific Reports, 1, 2.13% Scientific Reports 1 publication, 2.13%
Chem	Chem, 1, 2.13% Chem 1 publication, 2.13%
Journal of Fluorine Chemistry	Journal of Fluorine Chemistry, 1, 2.13% Journal of Fluorine Chemistry 1 publication, 2.13%
Tetrahedron Letters	Tetrahedron Letters, 1, 2.13% Tetrahedron Letters 1 publication, 2.13%
Israel Journal of Chemistry	Israel Journal of Chemistry, 1, 2.13% Israel Journal of Chemistry 1 publication, 2.13%
ChemInform	ChemInform, 1, 2.13% ChemInform 1 publication, 2.13%
Accounts of Chemical Research	Accounts of Chemical Research, 1, 2.13% Accounts of Chemical Research 1 publication, 2.13%
Natural Product Reports	Natural Product Reports, 1, 2.13% Natural Product Reports 1 publication, 2.13%
Synlett	Synlett, 1, 2.13% Synlett 1 publication, 2.13%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 1, 2.13% European Journal of Organic Chemistry 1 publication, 2.13%
Russian Chemical Reviews	Russian Chemical Reviews, 1, 2.13% Russian Chemical Reviews 1 publication, 2.13%
	1 2 3 4 5

Citations by publishers

	2 4 6 8 10 12 14 16
American Chemical Society (ACS)	American Chemical Society (ACS), 16, 34.04% American Chemical Society (ACS) 16 publications, 34.04%
Wiley	Wiley, 13, 27.66% Wiley 13 publications, 27.66%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 8, 17.02% Royal Society of Chemistry (RSC) 8 publications, 17.02%
Elsevier	Elsevier, 4, 8.51% Elsevier 4 publications, 8.51%
Shanghai Institute of Organic Chemistry	Shanghai Institute of Organic Chemistry, 1, 2.13% Shanghai Institute of Organic Chemistry 1 publication, 2.13%
Springer Nature	Springer Nature, 1, 2.13% Springer Nature 1 publication, 2.13%
Thieme	Thieme, 1, 2.13% Thieme 1 publication, 2.13%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 2.13% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 2.13%
	2 4 6 8 10 12 14 16

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Gao X., Zhang Y. J., Krische M. J. Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (α-Trifluoromethyl)allylation from the Alcohol or Aldehyde Oxidation Level // Angewandte Chemie - International Edition. 2011. Vol. 50. No. 18. pp. 4173-4175.

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RIS |

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RIS Copy

TY - JOUR

DO - 10.1002/anie.201008296

UR - https://doi.org/10.1002/anie.201008296

TI - Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (α-Trifluoromethyl)allylation from the Alcohol or Aldehyde Oxidation Level

T2 - Angewandte Chemie - International Edition

AU - Gao, Xin

AU - Zhang, Yong Jian

AU - Krische, Michael J

PY - 2011

DA - 2011/04/06 00:00:00

PB - Wiley

SP - 4173-4175

IS - 18

VL - 50

SN - 1433-7851

SN - 1521-3773

ER -

BibTex |

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@article{2011_Gao,

author = {Xin Gao and Yong Jian Zhang and Michael J Krische},

title = {Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (α-Trifluoromethyl)allylation from the Alcohol or Aldehyde Oxidation Level},

journal = {Angewandte Chemie - International Edition},

year = {2011},

volume = {50},

publisher = {Wiley},

month = {apr},

url = {https://doi.org/10.1002/anie.201008296},

number = {18},

pages = {4173--4175},

doi = {10.1002/anie.201008296}

}

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Gao, Xin, et al. “Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (α-Trifluoromethyl)allylation from the Alcohol or Aldehyde Oxidation Level.” Angewandte Chemie - International Edition, vol. 50, no. 18, Apr. 2011, pp. 4173-4175. https://doi.org/10.1002/anie.201008296.

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Publisher

Wiley

Journal

Angewandte Chemie - International Edition

Quartile SCImago

Quartile WOS

Impact factor

16.6

ISSN

14337851 (Print)
15213773 (Electronic)