Dearomative (3 + 2) Cycloaddition of Indoles for the Stereoselective Assembly of Fully Functionalized Cyclopentanoids.

Autor:	Qatran Al-Khdhairawi AA; Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281-S4, B-9000 Ghent, Belgium., Yuan T; Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281-S4, B-9000 Ghent, Belgium.; Yunnan Precious Metals Lab Co., Ltd, Keji Road 988, Kunming, Yunnan 650106, China., Van Hecke K; XStruct, Department of Chemistry, Ghent University, Krijgslaan 281-S3, B-9000 Ghent, Belgium., Winne JM; Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281-S4, B-9000 Ghent, Belgium.
Jazyk:	angličtina
Zdroj:	Organic letters [Org Lett] 2024 May 17; Vol. 26 (19), pp. 4077-4081. Date of Electronic Publication: 2024 May 02.
DOI:	10.1021/acs.orglett.4c01139
Abstrakt:	The gold(I)-catalyzed dearomative cyclopentannulation of various indoles with 2-ethynyl-1,3-dithiolane is reported. The method generates three new stereocenters with excellent control of relative stereochemistry and is tolerant of diverse functionalization and substitution patterns on the indoles. The obtained cyclopentane-fused indolines allow for interesting subsequent synthetic manipulations, giving rise to fully substituted cyclopentanes with control of the relative stereochemistry of all five stereocenters. The reported reaction illustrates and elucidates a mechanistic dichotomy underlying gold(I)-catalyzed reactions of 2-ethynyl-1,3-dithiolane.
Databáze:	MEDLINE
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