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  • Title: Highly enantioselective Friedel-Crafts reaction of thiophenes with glyoxylates: formal synthesis of duloxetine.
    Author: Majer J, Kwiatkowski P, Jurczak J.
    Journal: Org Lett; 2009 Oct 15; 11(20):4636-9. PubMed ID: 19764789.
    Abstract:
    An efficient Friedel-Crafts reaction of a series of 2-substituted thiophenes with alkyl glyoxylates has been developed using a catalytic amount of an easy accessible 6,6'-dibromo-BINOL/Ti(IV) complex. A variety of hydroxy(thiophene-2-yl)acetates can be synthesized in high enantioselectivites (92-98% ee) and good yields. This is the first report on the efficient asymmetric F-C reaction of thiophenes with alkyl glyoxylates. Starting from simple thiophene and n-butyl glyoxylate, we demonstrated the formal synthesis of duloxetine.
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