AI Article Synopsis
- - A new one-pot reaction method is created to efficiently synthesize complex tetrasubstituted cyclohexenes from basic unsaturated ketones or thioesters using a catalyst.
- - The process involves several steps, including the addition of trienolates to nitroolefins, followed by transformations that include double bond rearrangement and a unique cyclization reaction.
- - This approach achieves high selectivity in producing specific molecular structures while maintaining control over their stereochemistry, a significant advancement in organic synthesis.
Article Abstract
A catalyst-driven one-pot reaction sequence is developed for the enantio- and diastereoselective synthesis of tetrasubstituted cyclohexenes from simple unsaturated ketones or thioesters. The method involves a tertiary amine/squaramide-catalyzed α-selective addition of transiently generated trienolates to nitroolefins, subsequent base-catalyzed double bond isomerization, and an intramolecular (vinylogous) 1,6-addition reaction, a rare key carbocyclization step that proceeded with essentially perfect stereocontrol.
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| http://dx.doi.org/10.1002/anie.201908693 | DOI Listing |
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