Enantioselective cyclization of bromoenynes: mechanistic understanding of gold( i )-catalyzed alkoxycyclizations

Chemical Science 2026 Open access

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Authors: Andrea Cataffo, Eduardo Garcia-Padilla, Imma Escofet, Nicolás Fincias, Anna Arnanz, Giuseppe Zuccarello, Guilong Tian, Luyu Cai, Fereshteh Khorasani, Feliu Maseras, Antonio M. Echavarren
DOI: 10.1039/d5sc09023g
Cited by: 4
References: 88

Abstract

-chiral 2,5-diarylpyrrolidine unit. Using an achiral catalyst of the same family, the enantioselective cascade cyclization of bromo-1,5-enynes to form polycyclic scaffolds was also accomplished for the first time. Interestingly, performing the cyclization of bromo-1,6-enynes in the absence of an alcohol nucleophile led to the formation of nearly racemic cycloisomerization products. Control experiments and DFT calculations support a mechanism involving an in-cycle racemization process mediated by a 1,2-hydrogen shift, shedding new light on the mechanism of gold(i)-catalyzed alkoxycyclizations.

Fields of Study & Subjects

Catalytic Alkyne Reactions Catalytic C–H Functionalization Methods Organometallic Complex Synthesis and Catalysis

Publication details

Journal / source
Chemical Science
Publisher
Royal Society of Chemistry (RSC)
Volume
17
Issue
10
Pages
5005–5015
Publication date
1 January 2026
Language
EN