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

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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.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Stereoselective Synthesis of Functionalized Bicyclic Scaffolds by Passerini 3‐Center‐2‐Component Reactions of Cyclic Ketoacids ; volume:2017 ; number:9 ; year:2017 ; pages:1262-1271 ; extent:10
European journal of organic chemistry ; 2017, Heft 9 (2017), 1262-1271 (gesamt 10)

Creator: Cioc, Răzvan C.
Estévez, Verónica
van der Niet, Daan J.
Vande Velde, Christophe M. L.
Turrini, Nikolaus G.
Hall, Mélanie
Faber, Kurt
Ruijter, Eelco
Orru, Romano V. A.

DOI: 10.1002/ejoc.201601432

URN: urn:nbn:de:101:1-2022100308193012800634

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:23 AM CEST

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Cioc, Răzvan C.
Estévez, Verónica
van der Niet, Daan J.
Vande Velde, Christophe M. L.
Turrini, Nikolaus G.
Hall, Mélanie
Faber, Kurt
Ruijter, Eelco
Orru, Romano V. A.

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

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