Asymmetric Epoxidation Using Iminium Salt Organocatalysts Featuring Dynamically Controlled Atropoisomerism

作者:Page Philip C Bulman*; Bartlett Christopher J; Chan Yohan; Day David; Parker Phillip; Buckley Benjamin R; Rassias Geracimos A; Slawin Alexandra M Z; Allin Steven M; Lacour Jerome; Pinto Andre
来源:Journal of Organic Chemistry, 2012, 77(14): 6128-6138.
DOI:10.1021/jo300915u

摘要

Introduction of a pseudoaxial substituent at a stereogenic center adjacent to the nitrogen atom in binaphthyl- and biphenyl-derived azepinium salt organo-catalysts affords improved enantioselectivities and yields in the epoxidation of unfunctionalized alkenes. In the biphenyl-derived catalysts, the atropoisomerism at the biphenyl axis is controlled by the interaction of this substituent with the chiral substituent at nitrogen.

  • 出版日期2012-7-20