Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5283661 | Tetrahedron Letters | 2007 | 5 Pages |
Abstract
The reaction of chiral (2S)-enolates of dioxolan-4-ones, derived from lactic and mandelic acids, with (SR)-tert-butyl sulfinyl ketimines, derived from butan-2-one, pentan-2-one, and decan-2-one, afforded conformationally restrained β2,2,3,3-isoserines bearing two adjacent quaternary stereogenic centers in the form of N-sulfinyl protected 1â²-amino-dioxolan-4-ones. The selective acid-induced removal of the sulfinyl protecting group provided the corresponding 1â²-aminodioxolanones, whose base-induced cyclization afforded the corresponding chiral tetra-substituted 3-hydroxy-β-lactams. The synthesis of a dipeptide by reaction coupling between the 1â²-aminodioxolanone (2S,5R,1â²R)-19 and N,N-dimethylglycine was successfully achieved.
Keywords
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Andrea Guerrini, Greta Varchi, Cristian Samorì, Rizzo Daniele, Battaglia Arturo,