Vinyl azides Staudinger reaction

The absolute configuration of the structurally unique fungal metabolite mycosporins was determined in the laboratory of J.D. White by means of enantioselective total synthesis." In the endgame of the synthetic effort, the Staudinger reaction was used to elaborate the side chain. The cyclic vinyl azide was first converted to a stable vinyl iminophosphorane, which was subsequently reacted with benzyl glyoxylate to afford the corresponding Schiff base. Reduction of the imine was achieved with sodium cyanoborohydride. 

Sauers, R. R., Van Arnum, S. D. A Thio-Staudinger Reaction Thermolysis of a Vinyl Azide in the Presence of t-Butyl Mercaptan. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 2169-2181. 

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