{ALFA} Also catalyzes the ring-opening of 2

{ALF} Also catalyzes the ring-opening of 2,3-epoxy alcohols (e.g. from the above reactions) with various nucleophiles, including amines, thiols, thiolate anions, halides, carboxylates etc. The mild conditions result in increased regioselectivity: J. Org. Chem., 50, 1557 (1985).

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{ALF} Catalyst for transesterification, avoiding acidic or basic conditions. The reaction is carried out such that one alcohol is removed to displace the equilibrium: Synthesis, 138 (1982); Org. Synth. Coll., 8, 201 (1993). For application to carbamates, including Boc to Cbz conversion, see: J. Org. Chem., 62, 7096 (1997).

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{ALF} For a brief feature on uses of the reagent, see: Synlett, 2261 (2003).

{ALF} For conversion of epoxides to episulfides, see Thiourea, A12828. For use in reductive alkylation of amines, see Sodium cyanoborohydride, 87839. For use in enantioselective synthesis of homoallylic alcohols, see (R)-(+)-1,1'-Bi(2-naphthol)­, L08305. For reduction of amides to aldehydes, see Diphenyl­silane, A10884.

{ALF} For use in the Sharpless enantioselective epoxidation of allylic alcohols, see tert-Butyl­ hydroperoxide, A13926. For analogous enantioselective oxidation of sulfides to sulfoxides, see Cumene hydroperoxide, L06866. Epoxy alcohols can also be obtained in high yield in one pot by hydroperoxidation of alkenes with singlet oxygen in the presence of Ti(O-i-Pr)4: J. Am. Chem. Soc., 111, 203 (1989).

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