ChemInform Abstract: Glycono‐1,3‐lactams, xylo Series: Stereoselective Access by (2 + 2) Cycloaddition, Exploratory Transformations, and Discovery of a New, Highly Selective Inhibitor of Glucoamylases.

Abstract

Glycono-1,3-lactams, xylo Series: Stereoselective Access by (2 + 2) Cycloaddition, Exploratory Transformations, and Discovery of a New, Highly Selective Inhibitor of Glucoamylases. -Alkoxyacetylchlorides (I) and chiral imines (II) give lactams (III) with high diastereoselectivity. Several deprotection procedures are applied to these lactams to furnish the O,N-deprotected lactams. An unexpected fragmentation/rearrangement of lactam (IX) gives access to the rare class of 3,4-dihydro-2H-1,4-oxazin-3-ones (X)/(XI). -(KRAEMER, B.; FRANZ, T.; PICASSO, S.; PRUSCHEK, P.; JAEGER, V.; Synlett (1997) 3, 295-297; Inst. Org. Chem., Univ. Stuttgart,