Asymmetric, Three-Component, One-Pot Synthesis of Spiropyrazolones and 2,5-Chromenediones from Aldol Condensation/NHC-Catalyzed Annulation Reactions

作者:Wang Lei; Li Sun; Chauhan Pankaj; Hack Daniel; Philipps Arne R; Puttreddy Rakesh; Rissanen Kari; Raabe Gerhard; Enders Dieter
来源:Chemistry - A European Journal, 2016, 22(15): 5123-5127.
DOI:10.1002/chem.201600515

摘要

A novel one-pot, three-component diastereo- and enantioselective synthesis of spiropyrazolones has been developed involving the aldol condensation of an enal to generate ,-unsaturated pyrazolones, which react with a second equivalent of enal through an N-heterocyclic carbene (NHC)-catalyzed [3+2] annulation. The desired spirocyclopentane pyrazolones are obtained in moderate to good yields and good to excellent stereoselectivities. Alternatively, starting from cyclic 1,3-diketones, 2,5-chromenediones are available through [2+4] annulation.

  • 出版日期2016-4-4