Synfacts 2010(6): 0690-0690  
DOI: 10.1055/s-0029-1219976
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Phosphoramidite Ligands with an Acyclic TADDOL Backbone for Gold Catalysis

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
H. Teller, S. Flügge, R. Goddard, A. Fürstner*
Max-Planck-Institut für Kohlenforschung, Mülheim/Ruhr, Germany
Further Information

Publication History

Publication Date:
20 May 2010 (online)

Significance

In this paper the authors report the development of a new type of TADDOL-derived phosphoramidite gold catalysts. Thus, [2+2] cycloadditions were performed on a series of substrates with high yields and excellent enantioselectivities. Complex 1 appeared to be superior to the analogues 2 derived from standard TADDOL. This work presents the first example of a successful use of TADDOL derivatives containing an acyclic skeleton in asymmetric catalysis. Complex 1 also demonstrated high performance in the [4+2] cycloaddition of substrate 3.