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J Org Chem
; 89(13): 9420-9426, 2024 Jul 05.
Article
in English
| MEDLINE
| ID: mdl-38965937
ABSTRACT
Bifunctional thiourea-based organocatalysts facilitate an enantioselective desymmetrization and Lossen rearrangement cascade reaction of N-sulfoxy meso-succinimides, resulting in the synthesis of cyclic ß-amino acid derivatives. This catalytic system was optimized for bicyclic and tricyclic succinimide substrates affording yields from 61-91% and up to 96:4 er. This reaction proceeds via the group selective addition of the primary alcohol nucleophile to an enantiotopic carbonyl group with sequential rearrangement of the intermediate O-sulfonyl hydroxamate ester.