Schmidt Rearrangements of Hydroxyalkyl Azides toward Biologically Relevant Compounds

10 Schmidt Rearrangements of Hydroxyalkyl Azides toward Biologically Relevant Compounds 

A modular synthesis of a series of y-tum mimics was enabled by the Lewis acid-mediated reactions of enantiopnre hydroxyalkyl azides with piperidinones. This involved the preparation of enantiopnre azides 103, the side chains of which corresponded to those in natnrally occnrring side amino acids. These azides were combined with piperidinones 102 in the presence of BFs-OEta or TfOH, and the resulting imininm ethers hydrolyzed to the corresponding lactams 104 (Table 7.10). 

This chemistry was extended to the synthesis of libraries of snbstituted y-tnm-inspired molecnles by taking advantage of the ability to add nucleophiles to the intermediate 

60 compounds synthesized 39% average yield 91% average purity 

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