Diastereoselective synthesis of new zwitterionic bicyclic lactams, scaffolds for construction of 2-substituted-4-hydroxy piperidine and its pipecolic acid derivatives. Issue 7 (2nd February 2022)

• Record Type: Journal Article
• Authors: Reyes-Bravo, Enrique; Gnecco, Dino; Juárez, Jorge R.; Orea, María L.; Bernès, Sylvain; Aparicio, David M.; Terán, Joel L.
• Is Part Of: RSC advances. Volume 12:Issue 7(2022)
• Page Start: 4187
• Page End: 4190
• Publication Date: 2022-02-02
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d1ra09298g
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : The synthesis of new chiral highly functionalized zwitterionic bicyclic lactams starting from acyclic β-enaminoesters derived from ( R )-(−)-2-phenylglycinol is described. Abstract : The synthesis of new chiral highly functionalized zwitterionic bicyclic lactams starting from acyclic β-enaminoesters derived from ( R )-(−)-2-phenylglycinol is described. The key step involved an intramolecular non-classical Corey–Chaykovsky ring-closing reaction of the corresponding sulfonium salts derived from β-enaminoesters. This methodology permits the generation of two or three new stereogenic centers with high diastereoselectivity. The utility of these intermediates was demonstrated by the stereocontrolled total synthesis of cis -4-hydroxy-2-methyl piperidine and its corresponding pipecolic acid derivative.