345899-10-7Relevant academic research and scientific papers
Pyrrolidine N-oxides by stereoselective addition of Grignard and lithium compounds to 4,5-dideoxy-2,3-O-isopropylidene-D-erythro-4-pentenose N-benzyl nitrone and subsequent Cope-House cyclization
Palmer, Andreas M.,Jaeger, Volker
, p. 1293 - 1308 (2001)
The addition of Grignard reagents to D-erythro-4-pentenose N-benzyl nitrone 5, which is easily accessible from D-ribose, furnishes ω-unsaturated hydroxylamines that readily undergo Cope-House cyclization to afford pyrrolidine N-oxides. The stereoselectivity of the addition step is altered by either employing organolithium compounds or Lewis acids as complexing agents. The pyrrolidine N-oxides obtained by this sequence serve as key intermediates in the synthesis of 2,5-disubstituted pyrrolidine-3,4-diols (to be discussed in detail separately), both constituting new potential inhibitors of glycosidases.
