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Enantioselective Synthesis of Functionalized Diazaspirocycles from 4-Benzylideneisoxazol-5(4H)-one derivatives and Isocyanoacetate Esters

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Valencià Castellano

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Enantioselective Synthesis of Functionalized Diazaspirocycles from 4-Benzylideneisoxazol-5(4H)-one derivatives and Isocyanoacetate Esters

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Martínez-Pardo, Pablo; Laviós, Adrián; Sanz Marco, Amparo; Vila Descals, Carlos; Pedro, José Ramón; Blay Llinares, Gonzalo

Aquest document és un/a article, creat/da en: 2020

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.

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