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RSC Adv
; 12(7): 4187-4190, 2022 Jan 28.
Article
in English
| MEDLINE
| ID: mdl-35425406
ABSTRACT
The synthesis of new chiral highly functionalized zwitterionic bicyclic lactams starting from acyclic ß-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 ß-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.