Hydrazoic acid with epoxides

Glycidol (Eq, R98) hiu been treated with aqueoue sodium azide or aqueous hydrazoic acid. s> Approach of the reagent occurs toward the leaat-eubstituted epoxide carbon atom in both oases. The reaction of... 

Depazay and co-workers have described the synthesis of a series of polyhydroxylated pyrrolidine, piperidine and azepanes derived from D-mannitol as novel mimetics of somatostatin [8]. The synthesis of one piperidine 116 is shown in O Scheme 9. The authors used reaction of tr) tamine with the D-mannitol derived bis-epoxide 112 followed by protection of the indole nitrogen with a Boc group to prepare the L-gulo-piperidine 113, the azepane 114 also being formed. Selective protection of the primary alcohol followed by reaction with hydrazoic acid... 

In combination with methanol, azidotrimethylsilane was used to generate hydrazoic acid situ, and this in turn was responsible for ring opening of chiral epoxides derived from the tartaric... 

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