An organocatalytic approach to enantiomerically enriched α-arylcyclohexenones and cyclohexanonesDedicated to Amelia Tito on the occasion of her retirementElectronic supplementary information (ESI) available: Optimization of the Michael addition of 1 to crotonaldehyde and aromatic aldehydes; configurational assignment of 4a and 4a′, 8a, 9a and 10a; spectra; chiral HPLC conditions; X-ray crystallographic data of 7a and computational details. CCDC reference number 838553. For ESI and crystallograph

The presence of a p -nitrophenyl group converts acetone into an excellent and versatile nucleophile in organocatalytic processes, able to react with α,β-unsaturated aldehydes affording β-substituted α-arylcyclohexenones via a Michael reaction/aldol reaction/dehydration sequence, which occurs in good...

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Main Authors: Duce, Sara, Jorge, María, Alonso, Inés, Ruano, José Luis García, Cid, M. Belén
Format: Article
Language:English
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Summary:The presence of a p -nitrophenyl group converts acetone into an excellent and versatile nucleophile in organocatalytic processes, able to react with α,β-unsaturated aldehydes affording β-substituted α-arylcyclohexenones via a Michael reaction/aldol reaction/dehydration sequence, which occurs in good yields, ee up to 96% and complete diastereoselectivity. The resulting compounds are excellent synthons for the diastereoselective preparation of a variety of synthetically useful polysubstituted cyclohexanones and derivatives. The p -nitrophenyl group converts acetone into a versatile nucleophile that affords enantioenriched α-arylcyclohexenones via a Michael/aldol reaction/dehydration sequence.
ISSN:1477-0520
1477-0539
DOI:10.1039/c1ob06356a