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Stereoselective Synthesis of Functionalized Bicyclic Scaffolds by Passerini 3‐Center‐2‐Component Reactions of Cyclic Ketoacids
Author(s) -
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.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601432
Subject(s) - chemistry , stereoselectivity , isocyanide , isomerization , imide , bifunctional , bicyclic molecule , combinatorial chemistry , stereochemistry , organic chemistry , catalysis
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.