An organocatalytic approach to enantiomerically enriched alpha-arylcyclohexenones and cyclohexanones

作者:Duce Sara; Jorge Maria; Alonso Ines; Garcia Ruano Jose Luis; Belen Cid M
来源:Organic and Biomolecular Chemistry, 2011, 9(24): 8253-8260.
DOI:10.1039/c1ob06356a

摘要

The presence of a p-nitrophenyl group converts acetone into an excellent and versatile nucleophile in organocatalytic processes, able to react with alpha,beta-unsaturated aldehydes affording beta-substituted alpha-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.

  • 出版日期2011