Catalytic Asymmetric Synthesis of Epoxides from Aldehydes Using Sulfur Ylides with In Situ Generation of Diazocompounds

Abstract

A practical, general, and convergent route to epoxides with control of the relative and absolute stereochemistry has been achieved by generating the reactive intermediate (the diazo compound) in situ from tosylhydrazone salts (see scheme, PTC=phase-transfer catalyst, Ts=toluene-4-sulfonyl). High yields (58–82 %), high d.r. (88:12–98:2), and high ee values (87–94 %) have been obtained using a new class of stable chiral sulfides at low catalyst loading (5 mol %) and [Rh2(OAc)4] (0.5 mol %).