[5.5]-P-Spirocyclic Chiral Triaminoiminophosphorane-Catalyzed Asymmetric Hydrophosphonylation of Aldehydes and Ynones

作者:Uraguchi Daisuke; Ito Takaki; Kimura Yuto; Nobori Yumiko; Sato Makoto; Ooi Takashi*
来源:Bulletin of the Chemical Society of Japan, 2017, 90(5): 546-555.
DOI:10.1246/bcsj.20170040

摘要

Development of highly efficient and enantioselective hydrophosphonylations of aldehydes and ynones mediated by [5.5]P-spirocyclic chiral triaminoiminophosphoranes as base catalysts is described. The strong basicity of the iminophosphoranes and hydrogen-bond donating ability of their conjugate acids, tetraaminophosphonium ions, are critical for the facile generation of aminophosphonium phosphites with substantial nucleophilicity as well as for the subsequent selective, yet productive, P-C bond formation by suppressing undesired side reactions. The scope and limitations of these catalytic asymmetric methodologies are also reported.

  • 出版日期2017-5