Hydroxy alkylation glyoxylate

Subsequently, the same group reported an efficient AFC reaction of pyrroles having one electron-withdrawing group at the a,p or N-position with alkyl glyoxylates catalyzed by BINOL-Ti" complex 3 (Scheme 6.3). The reactions regioselectively afforded the desired pyrrole-hydroxy acetic acid derivatives 5 or 6 in good yields (up to 96%) and up to 97% ee. 

Friedel-Crafts alkylations of arenes with mesylates, benzyl or allyl alcohols, aldehyde/diol combinations (reductive alkylation), 1,3-dienes, or alkenes in an ionic liquid are also effectively catalyzed by Sc(OTf)3. Sc(OTf)3 works as an efficient catalyst for the condensation reaction of trimethylhydroquinone with isophytol to afford a-tocopherol. 2-Aminoalkylation of phenols with a-iminoacetates (or glyoxylate/amine) is catalyzed by Sc(OTf)3 to produce amino acid derivatives. The Sc(OTf)3-catalyzed alkylations of indoles with a-hydroxy esters, aziri-dines, acetals, and aldehydes have been utilized as key steps of total syntheses as exemplified in eq 15. ... 

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