Catalytic Asymmetric Conjugate Protosilylation and Protoborylation of 2-Trifluoromethyl Enynes for Synthesis of Functionalized Allenes.

Abstract

The Cu-catalyzed 1,4-protosilylation and protoborylation of trifluoromethyl-substituted conjugated enynes were developed to access functionalized homoallenylsilanes and homoallenylboronates. This protocol also provides a general method to synthesize optically active homoallenylsilanes and homoallenylboronates in moderate to excellent yields with high enantiomeric excess by using new designed chiral bisoxazoline ligands. Simultaneously, the transformations of homoallenylsilanes and homoallenylboronates were also explored to synthesize useful building blocks.