Structure determination of disease associated peak AAA from l-Tryptophan implicated in the eosinophilia-myalgia syndrome.

The eosinophilia-myalgia syndrome (EMS) outbreak of 1989 that occurred in the USA and elsewhere was caused by the ingestion of l-Tryptophan (L-Trp) solely manufactured by the Japanese company Showa Denko K.K. (SD).

Highly enantioselective iron(II)-catalyzed opening reaction of aromatic meso-epoxides with indoles.

A highly enantioselective method for the catalytic cis-stilbene oxide opening reaction with indole derivatives was developed. The scope of the reaction was studied with a selection of aromatic meso-epoxides and various indoles, and the desired 2-(indol-3-yl)ethanol derivatives were obtained in good to excellent yields with excellent enantioselectivities (from 96 to >99% ee).

Iron(II)-catalyzed enantioselective meso-epoxide-opening with anilines.

A highly enantioselective method for the catalytic opening of aromatic meso-epoxides with aniline derivatives was developed. The desired chiral β-amino alcohols were obtained in mostly good to very good yields with excellent enantioselectivities. Structural evidence of the pre-catalyst revealed a scarcely disclosed heptadentate Fe(II) complex with the chiral bipyridine ligand.

Highly enantioselective Mukaiyama aldol reaction in aqueous conditions using a chiral iron(II) bipyridine catalyst.

A highly enantioselective method for the catalytic Mukaiyama aldol reaction of silyl enol ethers with aldehydes in aqueous conditions was developed. The desired aldol products were obtained in excellent yields, diastereo- and enantioselectivities. Structural evidence of the pre-catalyst revealed an unprecedented heptadentate Fe(II) complex with the chiral bipyridine ligand.