Diastereoselective Synthesis of Cyclopenta[c]furans by a Catalytic Multicomponent Reaction. Issue 39 (19th August 2016)

• Record Type: Journal Article
• Authors: Pathipati, Stalin R.; van der Werf, Angela; Eriksson, Lars; Selander, Nicklas
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 39(2016)
• Page Start: 11863
• Page End: 11866
• Publication Date: 2016-08-19
• Subjects: alkynes -- enones -- fused-ring systems -- indium catalysis -- multicomponent reactions; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201606108
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A diastereoselective three‐component reaction between alkynyl enones, aldehydes and secondary amines is reported. With the aid of a benign indium catalyst, a range of highly substituted cyclopenta[ c ]furan derivatives can be obtained in a single‐step procedure. The formation of the stereodefined heterocyclic motifs takes place via in situ generation of enamines followed by two sequential cyclization steps. Abstract : A diastereoselective three‐component reaction between alkynyl enones, aldehydes and secondary amines is reported. With the aid of a benign indium catalyst, a range of highly substituted cyclopenta[ c ]furan derivatives is obtained in a single‐step procedure. The formation of the stereodefined heterocyclic motifs takes place through in situ generation of an enamine followed by two sequential cyclization steps.