Asymmetric Addition Reaction Using Sulfoximine Ligands

By: William Sommer, Aldrich ChemFiles 2008, 8.6, 9.

Aldrich ChemFiles 2008, 8.6, 9.

Chiral sulfoximine ligands have been studied for the past 15 years for catalytic asymmetric reactions. The Bolm group developed a new class of sulfoximine used with copper salts for asymmetric aldol reactions..1 Using these bidentate ligands, Bolm and co-workers reported up to 93% ee and 99% yield for the Mukaiyama-type aldol reaction of 1-phenyl-1-(trimethylsilyloxy)ethylene and methyl pyruvate (Scheme 1).

Scheme 1.

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  1. Okamura, H. et al. Chem. Lett. 2004, 33, 482.

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