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

Munoz-Herranz, Maria, Adrio, Javier, 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.

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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: Article
Faculty \ School: Faculty of Science > School of Chemistry
University of East Anglia > Faculty of Science > Research Groups > Synthetic Chemistry
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Depositing User: Rachel Smith
Date Deposited: 14 Feb 2012 16:22
Last Modified: 25 Jul 2018 06:36
URI: https://ueaeprints.uea.ac.uk/id/eprint/37113
DOI: 10.1021/om0491645

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