Bi(OTf)3‐Catalysed Access to 2, 3‐Substituted Isoindolinones and Tricyclic N, O‐Acetals by Trapping of Bis‐N‐Acyliminium Species in a Tandem Process. Issue 21 (24th June 2016)

• Record Type: Journal Article
• Authors: Aliyenne, Ahmed; Pin, Frédéric; Nimbarte, Vijaykumar D.; Lawson, Ata Martin; Comesse, Sébastien; Sanselme, Morgane; Tognetti, Vincent; Joubert, Laurent; Daïch, Adam
• Is Part Of: European journal of organic chemistry. Issue 21(2016)
• Page Start: 3592
• Page End: 3602
• Publication Date: 2016-06-24
• Subjects: Homogeneous catalysis -- Domino reactions -- Bismuth -- Carbocations -- Nitrogen heterocycles -- Oxygen heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600530
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : New 1, 3‐bis‐ N ‐acyliminium species generated easily with nontoxic Bi(OTf)3 catalyst at very low loadings (2 mol‐%) were trapped inter‐ and intramolecularly with various poly‐nucleophiles. This mild, efficient, practical and general tandem approach provides an array of substituted isoindolinones and cyclic N, O‐acetals. Abstract : Isoindolinones and tricyclic N, O‐acetals are obtained from bis‐ N ‐acyliminium precursors and assorted nucleophiles using catalytic Bi(OTf)3 . The reactions proceed, respectively, through a double amidoalkylation or tandem π‐cyclisation/α‐oxa‐amidoalkylation. Mechanistic aspects of the tandem chemistry are supported by DFT calculations and its utility in RCM and Click reactions illustrated.