Epoxides Bamford-Stevens reaction

Preparing the diazoalkane in situ by warming the sodium salt of the corresponding toluene-p-sulfonylhydrazone (Bamford-Stevens reaction, see Scheme 4.76) avoids isolation of the potentially explosive diazo compound. In the presence of a chiral sulfide the methodology has been applied to the asymmetric synthesis of epoxides (4.105). ... 

As mentioned previously, the Aggarwal group has utilized the Bamford-Stevens reaction as a method to in situ generate diazo compounds 33 and further trap out these in a subsequent reaction. This in situ concept was initially tested on the sulfur-ylide 37 mediated epoxidation of aldehydes 39. "... 

In Situ Bamford-Stevens Reaction Catalytic Synthesis of Epoxides (40) From Aldehydes Using Sulfur Ylides ... 

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