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Synfacts 2006(9): 0921-0921  
DOI: 10.1055/s-2006-949237
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

(R)-6,6′-Bis(CF3SO2)-binaphthol: A New Ligand for Asymmetric Synthesis

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
O. Mouhtady, H. Gaspard-Iloughmane, A. Laporterie, C. Le Roux*
Université Paul-Sabatier, Toulouse, France
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

The synthesis of a useful chiral BINOL-type ligand was reported. The ligand was tested in the Mannich reaction of 1-naphthalene-carboxaldehyde and the TMS-enol ether derived from methyl isobutyrate. The trifluoromethanesulfonyl group was deemed important for catalyst turnover. The use of Zr(Ot-Bu)4 or a 30 wt% solution of Zr(Oi-Pr)4 in i-PrOH gave good results.