Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines

作者:Smith Siobhan R; Fallan Charlene; Taylor James E; McLennan Ross; Daniels David S B; Morrill Louis C; Slawin Alexandra M Z; Smith Andrew D
来源:Chemistry - A European Journal, 2015, 21(29): 10530-10536.
DOI:10.1002/chem.201501271

摘要

A highly enantioselective Lewis base-catalysed formal [3+2] cycloaddition of ammonium enolates and oxaziridines to give stereodefined oxazolidin-4-ones in high yield is described. Employing an enantioenriched oxaziridine in this process leads to a matched/mis-matched effect with the isothiourea catalyst and allowed the synthesis of either syn- or anti-stereodefined oxazolidin-4-ones in high d.r., yield and ee. Additionally, the oxazolidin-4-one products have been derivatised to afford functionalised enantioenriched building blocks.

  • 出版日期2015-7-13