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- Title
Synthesis of Di-, Tri-, and Tetrasubstituted Oxetanes by Rhodium-Catalyzed OH Insertion and CC Bond-Forming Cyclization.
- Authors
Davis, Owen A.; Bull, James A.
- Abstract
Oxetanes offer exciting potential as structural motifs and intermediates in drug discovery and materials science. Here an efficient strategy for the synthesis of oxetane rings incorporating pendant functional groups is described. A wide variety of oxetane 2,2-dicarboxylates were accessed in high yields, including functionalized 3-/4-aryl- and alkyl-substituted oxetanes and fused oxetane bicycles. Enantioenriched alcohols provided enantioenriched oxetanes with complete retention of configuration. The oxetane products were further derivatized, while the ring was maintained intact, thus highlighting their potential as building blocks for medicinal chemistry.
- Subjects
RHODIUM catalyst selectivity; RING formation (Chemistry) kinetics; MATERIALS science; CHEMICAL alcohol synthesis; DERIVATIZATION
- Publication
Angewandte Chemie International Edition, 2014, Vol 53, Issue 51, p14230
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201408928