Sequential condensation and double desulfonylative cyclopropanation of 1,2-bis(sulfonylmethyl)arenes with 3-arylacroleins: access to biscyclopropane-fused tetralins

Efficient t BuOK-mediated sequential condensation and double desulfonylative cyclopropanation of readily accessible 1,2-bis(sulfonylmethyl)arenes with 3-arylacroleins is described. This high-yielding, single-step strategy provides a variety of polysubstituted biscyclopropane-fused tetralins with six...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2023-02, Vol.21 (6), p.126-1221
Main Authors: Hsueh, Nai-Chen, Wang, Yu-Han, Chang, Meng-Yang
Format: Article
Language:English
Subjects:
Aromatic compounds
Carbon
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Summary:Efficient t BuOK-mediated sequential condensation and double desulfonylative cyclopropanation of readily accessible 1,2-bis(sulfonylmethyl)arenes with 3-arylacroleins is described. This high-yielding, single-step strategy provides a variety of polysubstituted biscyclopropane-fused tetralins with six contiguous stereogenic centers via the construction of five carbon-carbon single bonds. A plausible mechanism is proposed and discussed. In the overall reaction process, water and sulfinic acid salts were generated as the byproducts. Efficient t BuOK-mediated sequential condensation and double desulfonylative cyclopropanation of 1,2-bis(sulfonylmethyl)arenes with 3-arylacroleins generates biscyclopropane-fused tetralins with six contiguous stereogenic centers in good yields.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob02188a