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Ligand Effects in Gold- and Platinum-Catalyzed Cyclization of Enynes: Chiral Gold Complexes for Enantioselective Alkoxycyclization

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Ligand Effects in Gold- and Platinum-Catalyzed Cyclization of Enynes: Chiral Gold Complexes for Enantioselective Alkoxycyclization. / Munoz-Herranz, Maria; Adrio, Javier; Carretero, Juan Carlos et al.
In: Organometallics, Vol. 24, No. 6, 12.02.2005, p. 1293-1300.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Munoz-Herranz, M, Adrio, J, Carretero, JC & Echavarren, AM 2005, 'Ligand Effects in Gold- and Platinum-Catalyzed Cyclization of Enynes: Chiral Gold Complexes for Enantioselective Alkoxycyclization', Organometallics, vol. 24, no. 6, pp. 1293-1300. https://doi.org/10.1021/om0491645

APA

Munoz-Herranz, M., Adrio, J., Carretero, J. C., & Echavarren, A. M. (2005). Ligand Effects in Gold- and Platinum-Catalyzed Cyclization of Enynes: Chiral Gold Complexes for Enantioselective Alkoxycyclization. Organometallics, 24(6), 1293-1300. https://doi.org/10.1021/om0491645

Vancouver

Munoz-Herranz M, Adrio J, Carretero JC, Echavarren AM. Ligand Effects in Gold- and Platinum-Catalyzed Cyclization of Enynes: Chiral Gold Complexes for Enantioselective Alkoxycyclization. Organometallics. 2005 Feb 12;24(6):1293-1300. doi: 10.1021/om0491645

Author

Munoz-Herranz, Maria ; Adrio, Javier ; Carretero, Juan Carlos et al. / Ligand Effects in Gold- and Platinum-Catalyzed Cyclization of Enynes: Chiral Gold Complexes for Enantioselective Alkoxycyclization. In: Organometallics. 2005 ; Vol. 24, No. 6. pp. 1293-1300.

Bibtex

@article{a31930d48e6e48daae48726252cd644e,
title = "Ligand Effects in Gold- and Platinum-Catalyzed Cyclization of Enynes: Chiral Gold Complexes for Enantioselective Alkoxycyclization",
abstract = "Phosphine and bidentate N-N ligands inhibit the Alder-ene-type cycloisomerization of enynes catalyzed by Pt(II) and favor the alkoxycyclization process. The enantioselective Pt(II)-catalyzed alkoxycyclization has been studied in the presence of chiral mono- and bidentate phosphines, as well as chiral bidentate N-N ligands. Modest levels of enantioselection (up to 50% ee) have been obtained with Tol-BINAP as ligand. The alkoxycyclizations with a catalyst formed from [Au(L)Cl]/AgX proceed more readily, and up to 94% ee's have been obtained using [(AuCl)2(Tol-BINAP)] (47) as the precatalyst. The X-ray crystal structures of Au(I) complexes 47 and chloro-(R)-2-(tert-butylsulfenyl)-1-(diphenylphosphino)ferrocene gold(I) (39) show the AuCl fragments monocoordinated with the P centers of the chiral phosphine ligands.",
author = "Maria Munoz-Herranz and Javier Adrio and Carretero, {Juan Carlos} and Echavarren, {Antonio M.}",
year = "2005",
month = feb,
day = "12",
doi = "10.1021/om0491645",
language = "English",
volume = "24",
pages = "1293--1300",
journal = "Organometallics",
issn = "0276-7333",
publisher = "American Chemical Society",
number = "6",

}

RIS

TY - JOUR

T1 - Ligand Effects in Gold- and Platinum-Catalyzed Cyclization of Enynes: Chiral Gold Complexes for Enantioselective Alkoxycyclization

AU - Munoz-Herranz, Maria

AU - Adrio, Javier

AU - Carretero, Juan Carlos

AU - Echavarren, Antonio M.

PY - 2005/2/12

Y1 - 2005/2/12

N2 - Phosphine and bidentate N-N ligands inhibit the Alder-ene-type cycloisomerization of enynes catalyzed by Pt(II) and favor the alkoxycyclization process. The enantioselective Pt(II)-catalyzed alkoxycyclization has been studied in the presence of chiral mono- and bidentate phosphines, as well as chiral bidentate N-N ligands. Modest levels of enantioselection (up to 50% ee) have been obtained with Tol-BINAP as ligand. The alkoxycyclizations with a catalyst formed from [Au(L)Cl]/AgX proceed more readily, and up to 94% ee's have been obtained using [(AuCl)2(Tol-BINAP)] (47) as the precatalyst. The X-ray crystal structures of Au(I) complexes 47 and chloro-(R)-2-(tert-butylsulfenyl)-1-(diphenylphosphino)ferrocene gold(I) (39) show the AuCl fragments monocoordinated with the P centers of the chiral phosphine ligands.

AB - Phosphine and bidentate N-N ligands inhibit the Alder-ene-type cycloisomerization of enynes catalyzed by Pt(II) and favor the alkoxycyclization process. The enantioselective Pt(II)-catalyzed alkoxycyclization has been studied in the presence of chiral mono- and bidentate phosphines, as well as chiral bidentate N-N ligands. Modest levels of enantioselection (up to 50% ee) have been obtained with Tol-BINAP as ligand. The alkoxycyclizations with a catalyst formed from [Au(L)Cl]/AgX proceed more readily, and up to 94% ee's have been obtained using [(AuCl)2(Tol-BINAP)] (47) as the precatalyst. The X-ray crystal structures of Au(I) complexes 47 and chloro-(R)-2-(tert-butylsulfenyl)-1-(diphenylphosphino)ferrocene gold(I) (39) show the AuCl fragments monocoordinated with the P centers of the chiral phosphine ligands.

U2 - 10.1021/om0491645

DO - 10.1021/om0491645

M3 - Journal article

VL - 24

SP - 1293

EP - 1300

JO - Organometallics

JF - Organometallics

SN - 0276-7333

IS - 6

ER -