Studies on cyclization reactions of 3-amino-2, 4-dihydroxybutanoic acid derivatives. Issue 6 (20th January 2017)

• Record Type: Journal Article
• Authors: Esgulian, Mathieu; Belot, Vincent; Guillot, Régis; Deloisy, Sandrine; Aitken, David J.
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 6(2017)
• Page Start: 1453
• Page End: 1462
• Publication Date: 2017-01-20
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob02759h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Linear derivatives of the title compound are convenient precursors for regioselective cyclizations leading to highly-functionalized γ-lactones, oxazolidinones, oxazolines and aziridines. Abstract : A number of cyclic derivatives of 3-amino-2, 4-dihydroxybutanoic acid are known in the literature but they are often prepared from other cyclic precursors. This study showed that the title compound too may serve as a convenient substrate for cyclization reactions. Using orthogonally-protected linear derivatives, regioselective cyclizations were performed, leading to original and highly-functionalized γ-lactones, oxazolidinones, oxazolines and aziridines. In these reactions a key role was played by the C3 nitrogen group function, while the C2 alcohol function showed no propensity for participation in cyclization reactions.