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

Munoz-Herranz, Maria and Adrio, Javier and Carretero, Juan Carlos and Echavarren, Antonio M. (2005) Ligand Effects in Gold- and Platinum-Catalyzed Cyclization of Enynes: Chiral Gold Complexes for Enantioselective Alkoxycyclization. Organometallics, 24 (6). pp. 1293-1300. ISSN 0276-7333

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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.

Item Type:
Journal Article
Journal or Publication Title:
Organometallics
Uncontrolled Keywords:
Research Output Funding/yes_externally_funded
Subjects:
?? yes - externally fundedorganic chemistryphysical and theoretical chemistryinorganic chemistry ??
ID Code:
185739
Deposited By:
Deposited On:
03 Feb 2023 15:15
Refereed?:
Yes
Published?:
Published
Last Modified:
15 Jul 2024 23:31