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

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...

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Veröffentlicht in:European journal of organic chemistry Jg. 2017; H. 9; S. 1262 - 1271
Hauptverfasser: 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.
Format: Journal Article
Sprache:Englisch
Veröffentlicht: WEINHEIM Wiley 03.03.2017
Wiley Subscription Services, Inc
John Wiley and Sons Inc
Schlagworte:
Chemistry
Chemistry, Organic
Cyclization
Diastereoselectivity
Ketoacids
Lactones
Multicomponent reactions
Physical Sciences
Rearrangement
Science & Technology
Multicomponent reactions
ACID
Cyclization
Ketoacids
DIASTEREOSELECTIVE SYNTHESIS
HETEROCYCLES
ISOCYANIDES
UGI-REACTION
FACILE
Diastereoselectivity
Lactones
Rearrangement
ISSN:1434-193X, 1099-0690
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Zusammenfassung: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. The use of cyclic ketoacids as bifunctional starting materials in diastereoselective Passerini three‐center‐two‐component reactions is reported. The resulting trans‐fused α‐carboxamido lactones were found to be readily converted into cis‐fused bicyclic α‐hydroxy imides under acidic conditions. Enantioenriched Passerini products can be obtained by using a chemoenzymatically generated ketoacid.
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ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201601432