Abstract
We have developed Pd-catalyzed intermolecular Friedel-Crafts-type allylic alkylation and allylic dearomatization reactions of substituted indoles bearing a nucleophilic group with vinyloxirane, providing an efficient method to synthesize structurally diverse tetrahydrocarboline and spiroindolenine derivatives under mild conditions.
Highlights
We have developed Pd-catalyzed intermolecular Friedel–Craftstype allylic alkylation and allylic dearomatization reactions of substituted indoles bearing a nucleophilic group with vinyloxirane, providing an efficient method to synthesize structurally diverse tetrahydrocarboline and spiroindolenine derivatives under mild conditions
Substituted indole nucleus and polycyclic skeletons embedded with indoline moieties represent important structural motifs in numerous natural products and pharmaceuticals.[1]
Allylic alcohols as electrophiles in allylic substitution reactions in the presence of suitable promoters were reported in the last decade.[4]
Summary
Pd-catalyzed cascade allylic alkylation and dearomatization reactions of indoles with vinyloxirane† We have developed Pd-catalyzed intermolecular Friedel–Craftstype allylic alkylation and allylic dearomatization reactions of substituted indoles bearing a nucleophilic group with vinyloxirane, providing an efficient method to synthesize structurally diverse tetrahydrocarboline and spiroindolenine derivatives under mild conditions. Substituted indole nucleus and polycyclic skeletons embedded with indoline moieties represent important structural motifs in numerous natural products and pharmaceuticals.[1] transition-metal catalyzed Friedel–Crafts-type allylic alkylation[2] and allylic dearomatization[3] reactions of indoles have proved to be efficient and successful strategies for the synthesis of structurally diverse indolines in good yields with high diastereoselectivity and enantioselectivity.
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