Synthesis of Chiral, Densely Substituted Pyrrolidones via Phosphine-Catalyzed Cycloisomerization

Synthesis of Chiral, Densely Substituted Pyrrolidones via Phosphine-Catalyzed Cycloisomerization

Densely substituted chiral pyrrolidones are synthesized via phosphine-catalyzed cycloisomerization of enantioenriched β-amino ynones, which are prepared in a single step using a highly enantioselective Zn-ProPhenol-catalyzed Mannich reaction. The exocyclic alkenes in the cyclization products provide...

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Veröffentlicht in:Organic letters 2019-03, Vol.21 (6), p.1890-1894
Hauptverfasser: Trost, Barry M, Gnanamani, Elumalai, Hung, Chao-I Joey, Kalnmals, Christopher A
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container_end_page 1894
container_issue 6
container_start_page 1890
container_title Organic letters
container_volume 21
creator Trost, Barry M
Gnanamani, Elumalai
Hung, Chao-I Joey
Kalnmals, Christopher A
description Densely substituted chiral pyrrolidones are synthesized via phosphine-catalyzed cycloisomerization of enantioenriched β-amino ynones, which are prepared in a single step using a highly enantioselective Zn-ProPhenol-catalyzed Mannich reaction. The exocyclic alkenes in the cyclization products provide versatile handles for further transformations and typically form with good E/Z selectivity. This cycloisomerization method can be performed in streamlined fashion, without purification of the intermediate Mannich adduct, and extends to anthranilic acid based scaffolds in addition to ProPhenol-derived Mannich adducts.
doi_str_mv 10.1021/acs.orglett.9b00496
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title Synthesis of Chiral, Densely Substituted Pyrrolidones via Phosphine-Catalyzed Cycloisomerization
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