6533b7d0fe1ef96bd125b763
RESEARCH PRODUCT
Enantioselective Synthesis of Functionalized Diazaspirocycles from 4‐Benzylideneisoxazol‐5(4H)‐one Derivatives and Isocyanoacetate Esters
Carlos VilaAmparo Sanz-marcoPablo Martínez-pardoAdrián LaviósJosé R. PedroGonzalo Blaysubject
CatàlisiCompostos orgànicsChemistryEnantioselective synthesisGeneral ChemistryQuímica orgànicaCombinatorial chemistryCycloadditiondescription
Enantioenriched spirocyclic compounds bearing three contiguous stereocenters and high functionalization were obtained through a formal [3+2] cycloaddition reaction catalyzed by a cooperative system. The spiro compounds were synthesized from 4-arylideneisoxazol-5-ones and isocyanoacetate esters using a bifunctional squaramide/Brønsted base organocatalyst derived from a Cinchona alkaloid and silver oxide as Lewis acid. This method afforded two out of the four possible diastereomers with good yields and high enantiomeric excess for both diastereomers.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2020-07-16 | Advanced Synthesis & Catalysis |