Use of Planar Chiral Ferrocenyl­phosphine‐Gold(I) Complexes in the Asymmetric Cycloisomerization of 3‐Hydroxylated 1, 5‐Enynes. Issue 1 (30th November 2015)

• Record Type: Journal Article
• Authors: Wu, Zhiyong; Retailleau, Pascal; Gandon, Vincent; Voituriez, Arnaud; Marinetti, Angela
• Is Part Of: European journal of organic chemistry. Issue 1(2016)
• Page Start: 70
• Page End: 75
• Publication Date: 2015-11-30
• Subjects: Asymmetric catalysis -- Cycloisomerization -- Homogeneous catalysis -- Gold -- Ligand design -- P ligands; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201501121
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Chiral monodentate phosphines based on ortho ‐disubstituted ferrocene units have been prepared and used for the synthesis of gold(I) complexes. These complexes are highly active catalysts for the cycloisomerization of 3‐hydroxy‐1, 5‐enynes into bicyclo[3.1.0]hexanones. Their high catalytic activity is ascribed to their structural analogy to the biaryl‐based Buchwald phosphines. This paper discloses the first enantioselective variant of these reactions based on gold catalysis ( ee 's up to 80 %). Abstract : Chiral monodentate phosphines have been prepared and used for the synthesis of gold(I) complexes. These complexes proved to be highly active catalysts for the first enantioselective gold‐catalysed cycloisomerization reactions of 3‐hydroxy‐1, 5‐enynes ( ee 's up to 80 %).