New polyhydroxylated pyrrolidines derived from enantiopure 3,6-dihydro-2H-1,2-oxazines.
[reaction: see text] Diastereoselective hydroborations of enantiopure 3,6-dihydro-2H-1,2-oxazines led to dihydroxy-substituted 1,2-oxazines. Samarium diiodide-induced N-O bond cleavage generated 1,4-amino alcohols which were recyclized to polyhydroxylated pyrrolidines which are potential glycosidase inhibitors.
Pulz
Robert
R
Institut für Chemie - Organische Chemie, Freie Universität Berlin, Takustrasse 3, D-14195 Berlin, Germany.
Al-Harrasi
Ahmed
A
Reissig
Hans-Ulrich
HU