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Synlett
DOI: 10.1055/a-2319-3343
letter

Organocatalytic [3+2] annulation of β-tetralones with α, β-unsaturated aldehydes

Zheyao Li
1   School of Pharmacy, East China University of Science and Technology, Shanghai, China (Ringgold ID: RIN47860)
,
Xinzhe Zhang
1   School of Pharmacy, East China University of Science and Technology, Shanghai, China (Ringgold ID: RIN47860)
,
Jiawei Yu
1   School of Pharmacy, East China University of Science and Technology, Shanghai, China (Ringgold ID: RIN47860)
,
Huiwen Zhang
2   WuXi AppTec Shanghai Co Ltd, WuXi AppTec Shanghai Co Ltd, Shanghai, China (Ringgold ID: RIN118284)
,
Xinhong Yu 
1   School of Pharmacy, East China University of Science and Technology, Shanghai, China (Ringgold ID: RIN47860)
› Author AffiliationsSupported by: National Natural Science Foundation of China 21476078
Supported by: Science and Technology Commission of Shanghai Municipality 12431900902
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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 as an identical twin electron donor-acceptors, and the Cβ and Cα of enals as the heterogenous 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 in mild condition and without the use of transition metals.



Publication History

Received: 03 April 2024

Accepted after revision: 03 May 2024

Accepted Manuscript online:
03 May 2024

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