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Stereoselective Synthesis of Functionalized Bicyclic Scaffolds by Passerini 3-Center-2-Component Reactions of Cyclic Ketoacids.

ABSTRACT: We report the use of bifunctional starting materials (ketoacids) in a diastereoselective Passerini three-center-two-component reaction. Study of the reaction scope revealed the required structural features for stereoselectivity in the isocyanide addition. In this system, an interesting isomerization of the primary Passerini product - the α-carboxamido lactone - into an atypical product, an α-hydroxy imide, was found to occur under acidic conditions. Furthermore, enantioenriched Passerini products can be generated from an enantioenriched ketoacid obtained by chemoenzymatic synthesis.

SUBMITTER: Cioc RC

PROVIDER: S-EPMC5347843 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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Stereoselective Synthesis of Functionalized Bicyclic Scaffolds by Passerini 3-Center-2-Component Reactions of Cyclic Ketoacids.

Cioc Răzvan C RC Estévez Verónica V van der Niet Daan J DJ Vande Velde Christophe M L CM Turrini Nikolaus G NG Hall Mélanie M Faber Kurt K Ruijter Eelco E Orru Romano V A RV

European journal of organic chemistry 20170308 9

We report the use of bifunctional starting materials (ketoacids) in a diastereoselective Passerini three-center-two-component reaction. Study of the reaction scope revealed the required structural features for stereoselectivity in the isocyanide addition. In this system, an interesting isomerization of the primary Passerini product - the α-carboxamido lactone - into an atypical product, an α-hydroxy imide, was found to occur under acidic conditions. Furthermore, enantioenriched Passerini product ...[more]

PMID: 28344504

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