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DOI: 10.1055/a-2319-3343
Organocatalytic [3+2] Annulation of β-Tetralones with α,β-Unsaturated Aldehydes
We gratefully acknowledge financial support from the National Natural Science Foundation of China (21476078) and the Science and Technology Commission of Shanghai Municipality (12431900902).
Abstract
The NBS-mediated organocatalytic cascade synthesis of 4,5-dihydronaphtho[2,1-b]furan-1-carbaldehydes from α,β-unsaturated aldehydes and 2-tetralones have been developed. In this synthesis strategy, the C1 of in situ generated brominated 2-tetralone was used as identical twin electron donor–acceptor, and the Cβ and Cα of enals were used as the heterogeneous twin electron acceptor–donors. The process has been realized by a synergistic amine/p-TSA catalyzed one-pot cascade Michael addition–cyclopropanation–ring opening–oxa-Michael addition under mild conditions and without the use of transition metals.
Key words
organocatalysis - cascade reaction - [3+2] annulation - 2-tetralone - 4,5-dihydronaphtho[2,1-b]furanSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2319-3343.
- Supporting Information
Publication History
Received: 03 April 2024
Accepted after revision: 03 May 2024
Accepted Manuscript online:
03 May 2024
Article published online:
03 June 2024
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- 24 General Procedures for [3+2] Annulation Reaction a (1.0 mmol, 1.0 equiv), NBS (1.1 mmol, 1.1 equiv) and p-TSA (0.1 mmol, 0.1 equiv) were added to 5 mL CHCl3 sequentially and stirred at 25 °C. When a was transformed completely in almost 20 min, b (0.8 mmol, 0.8 equiv), NaOAc (2.0 mmol, 2.0 equiv), and Cat. I (0.2 mmol, 0.2 equiv) were added sequentially to the mixture and stirred at 60 °C. When the reaction was completed, the reaction mixture was filtered and concentrated under reduce pressure. The residue was purified by silica gel column chromatography using a 200:1 mixture of petrol ether/ethyl acetate.