Anti-Selective Vicinal Silaboration and Diboration of Alkynoates through Phosphine Organocatalysis

作者:Nagao Kazunori; Ohmiya Hirohisa*; Sawamura Masaya
来源:Organic Letters, 2015, 17(5): 1304-1307.
DOI:10.1021/acs.orglett.5b00305

摘要

Trialkylphosphine organocatalysts have enabled anti-selective vicinal silaboration and diboration of the C-C triple bond in alkynoates to produce beta-boryl-alpha-silyl acrylates and alpha,beta-diboryl acrylates, respectively. The anti stereoselectivity was complete and robust. A variety of functional groups were tolerated in the alkynoates. The two vicinally installed heteroatom substituents of the beta-boryl-alpha-silyl acrylates and alpha,beta-diboryl acrylates could be differentiated and transformed in a stepwise manner, allowing the synthesis of a diverse array of unsymmetrical tetrasubstituted alkenes.

  • 出版日期2015-3-6