Asymmetric Alkynylation/Lactamization Cascade: An Expeditious Entry to Enantiomerically Enriched Isoindolinones |
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Authors: | Dr. Vishnumaya Bisai Arun Suneja Prof. Dr. Vinod K. Singh |
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Affiliation: | 1. Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal, M.P. – 462 066 (India);2. Indian Institute of Technology, Kanpur, U.P. – 208?016 (India) |
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Abstract: | An unprecedented CuI–pybox‐diPh‐catalyzed highly enantioselective (up to >99 % ee) alkynylation/lactamization cascade has been developed as a general catalytic system for the synthesis of diversely substituted isoindolinones of immense biological importance. The cascade effects one C? C and two C? N bond‐forming events in one reaction vessel under operationally simple, additive‐free reaction conditions in good to excellent yields. The methodology was further extended to the synthesis of tetrahydroisoquinoline scaffolds common to several biologically active natural products in a two‐step sequence with remarkable selectivity (up to 94 % ee). |
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Keywords: | alkynylation domino reactions isoindolinones synthetic methods tetrahydroisoquinolines |
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