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 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.
Department of Chemistry and Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS) Vrije Universiteit Amsterdam De Boelelaan 1108 1081 HZ Amsterdam The Netherlands.
Răzvan C
RC
Cioc
Department of Chemistry and Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS) Vrije Universiteit Amsterdam De Boelelaan 1108 1081 HZ Amsterdam The Netherlands.
Verónica
V
Estévez
Department of Chemistry and Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS) Vrije Universiteit Amsterdam De Boelelaan 1108 1081 HZ Amsterdam The Netherlands.
Daan J
DJ
van der Niet
Faculty of Applied Engineering University of Antwerp Groenenborgerlaan 171 2020 Antwerpen Belgium.
Christophe M L
CM
Vande Velde
Department of Chemistry University of Graz Heinrichstrasse 28 8010 Graz Austria.
Nikolaus G
NG
Turrini
Department of Chemistry University of Graz Heinrichstrasse 28 8010 Graz Austria.
Mélanie
M
Hall
Department of Chemistry University of Graz Heinrichstrasse 28 8010 Graz Austria.
Kurt
K
Faber
Department of Chemistry and Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS) Vrije Universiteit Amsterdam De Boelelaan 1108 1081 HZ Amsterdam The Netherlands.
Eelco
0000-0002-1105-3947
E
Ruijter
Department of Chemistry and Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS) Vrije Universiteit Amsterdam De Boelelaan 1108 1081 HZ Amsterdam The Netherlands.
Romano V A
RV
Orru
Cyclization; Diastereoselectivity; Ketoacids; Lactones; Multicomponent reactions; Rearrangement