Synthesis of Polysubstituted Fused Pyrroles by Gold-Catalyzed Cycloisomerization/1,2-Sulfonyl Migration of Yndiamides | Zendy

Philip CameronSmith | Zendy; Yubo Jiang | Zendy; Zixuan Tong | Zendy; Helena D. Pickford | Zendy; Kirsten E. Christensen | Zendy; Jeremy Nugent | Zendy; Edward A. Anderson | Zendy

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Synthesis of Polysubstituted Fused Pyrroles by Gold-Catalyzed Cycloisomerization/1,2-Sulfonyl Migration of Yndiamides

Author(s) -

Philip CameronSmith,

Yubo Jiang,

Zixuan Tong,

Helena D. Pickford,

Kirsten E. Christensen,

Jeremy Nugent,

Edward A. Anderson

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.1c02360

Subject(s) - cycloisomerization , chemistry , sulfonyl , catalysis , combinatorial chemistry , pyrrole , organic chemistry , alkyl

Yndiamides (bis-N-substituted alkynes) are valuable precursors to azacycles. Here we report a cycloisomerization/1,2-sulfonyl migration of alkynyl-yndiamides to form tetrahydropyrrolopyrroles, unprecedented heterocyclic scaffolds that are relevant to medicinal chemistry. This functional group tolerant transformation can be achieved using Au(I) catalysis that proceeds at ambient temperature, and a thermally promoted process. The utility of the products is demonstrated by a range of reactions to functionalize the fused pyrrole core.

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