Highly diastereoselective C → N acyl rearrangement in polysubstituted pyrrolidine 2, 2-dicarboxylates. Stereocontrolled synthesis of densely functionalized prolines. Issue 6 (20th December 2017)

• Record Type: Journal Article
• Authors: Reboredo, Silvia; García-Marijuan, Ainara; Uria, Uxue; Reyes, Efraím; Carrillo, Luisa; Ugarriza, Iratxe; Vicario, Jose L.
• Is Part Of: Organic chemistry frontiers. Volume 5:Issue 6(2018)
• Page Start: 933
• Page End: 942
• Publication Date: 2017-12-20
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c7qo00793k
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A fully diastereoselective C–N acyl transfer reaction operates in enantiopure densely substituted pyrrolidine 2, 2-dicarboxylates. Abstract : An efficient and easy protocol for promoting a C → N acyl transfer reaction in diverse enantiopure densely substituted pyrrolidine 2, 2-dicarboxylates was performed, yielding the corresponding proline ester derivatives with yields in the range of 68–99% and total diastereoselection (dr > 95 : 5 in all cases). The substitution patterns both at C-3 and C-5 present in starting pyrrolidines as well as the viability of presenting different alkoxycarbonyl moieties have been evaluated observing good reaction performance in all cases.