Methods for stereoselective polyene cyclization
By using an acidic sulfonamide Brønsted acid catalyst, the reaction of compounds with formula (II) solves the problems of low efficiency and poor selectivity in the production of ambroxol and succinyl lactone in the prior art, and realizes the synthesis of tricyclic compounds with high yield and high selectivity.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- BASF SE
- Filing Date
- 2024-10-31
- Publication Date
- 2026-05-29
AI Technical Summary
Existing technologies are difficult to efficiently and enantioselectively produce ambroxol and succinyl lactone from readily available precursors such as citral and nerolidol. Furthermore, existing methods require highly corrosive acids, low temperatures, and toxic solvents, or rely on expensive enzymatic catalysts.
A catalytic amount of acidic sulfonamide-based Brønsted acid catalyst is used to react a compound having formula (II) under specific conditions to form a tricyclic compound having formula (I), including the use of an acidic sulfonamide moiety having 1 to 20 carbon atoms as a catalyst.
It achieves high yield and good diastereoselectivity, forming diastereomers mainly linked by trans, with yields typically >30%, trans:cis ratio >80:20, and forming all-trans diastereomers to epi-diastereomers in a ratio >1:1, avoiding unwanted cis isomers.
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Figure CN122122137A_ABST