Asymmetric aza-Michael addition under ultra-high pressure: Short bias to polyhydroxylated piperidines

Article abstract of DOI:10.1039/c1gc15097a

Two polyhydroxylated piperidines have been prepared in short sequences from diacetone gluco- and allofuranose. The key step is a piezo-aza-Michael addition of diphenylmethanamine to enoates bearing a sugar moiety in the γ-position. The combination of ultra-high pressure associated to the presence of readily available sugars chiral pool led to the expected chiral amines in good yields and excellent stereoselectivities.