An efficient synthesis of aminocyclopentitols via the stereoselective amination of polybenzyl ethers using chlorosulfonyl isocyanate

摘要

An efficient stereoselective route for the preparation of stereoisomeric aminocyclopentitols 3-5 was achieved using a six-step sequence starting from the corresponding D-sugars. Key steps of the synthesis of the title compounds involved the regioselective and diastereoselective amination of cinnamylic 1,2-anti- or 1,2-syntribenzyl ethers using, chlorosulfonyl isocyanate (CSI), intramolecular olefin metathesis. and diastereoselective dihydroxylation.