New camphor-derived selenonium ylides: Enantioselective synthesis of chiral epoxides

Article abstract of DOI:10.1071/CH05157

Optically pure selenonium salts 3 as the precursors of two new chiral selenonium ylides 4 can be synthesized stereoselectively from natural d-camphor in good yields. It is found that the reaction of the selenonium salt 3b, an aldehyde, and potassium tert-butoxide can take place smoothly in ?one-pot' via the formation of selenonium ylide 4b, to give chiral trans-diaryl epoxides 5 in good yields with good diastereoselectivities and enantioselectivities. CSIRO 2005.