A selective and rapid access to six-or seven-membered ring iminosugars is reported. The key step of the strategy involves the highly regio-and stereoselective reduction of 6,8-diazabicyclo[3.2.1]oct-6-ene intermediates, depending on the nature of imine substituents.
Hexahydro -3-phenyl-6,7,8-trihydroxy-3R-[3α,5β,6β,7α,8β,8aβ]-5H-oxazolo[3,2-a]pyridine-5-carbonitrile is endowed with two non equivalent reactive sites: an α-amino nitrile at the C-5 position and an α-amino ether at the C-8a position. Herein, alkylation at the C-5 position was studied. The scope and limitations of these reactions have been investigated.
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