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Asymmetric Alkynylation/Lactamization Cascade: An Expeditious Entry to Enantiomerically Enriched Isoindolinones
Author(s) -
Bisai Vishnumaya,
Suneja Arun,
Singh Vinod K.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201405074
Subject(s) - enantioselective synthesis , alkynylation , chemistry , cascade , catalysis , tetrahydroisoquinoline , selectivity , combinatorial chemistry , reaction conditions , cascade reaction , organocatalysis , sequence (biology) , organic chemistry , stereochemistry , biochemistry , chromatography
An unprecedented Cu I –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 CC and two CN 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 ).