posted on 2021-10-26, 16:49authored byGuofeng Zhao, Yi Wu, Hai-Hong Wu, Junfeng Yang, Junliang Zhang
Significant attention has been given
in the past few years to the
selective transformations of N-tosylhydrazones to
various useful compounds. However, the development of enantioselective
versions poses considerable challenges. Herein we report a Pd-catalyzed
enantioselective three-component coupling of N-tosylhydrazone,
aryl halide, and terminal alkyne under mild conditions utilizing a
novel chiral sulfinamide phosphine ligand (GF-Phos),
which provides a facile access to chiral diarylmethyl alkynes, which
are useful synthons in organic synthesis as well as exist as the skeleton
in many bioactive molecules. A pair of enantiomers of the product
could be easily prepared using the same chiral ligand by simply changing
the aryl substituents of the N-tosylhydrazone and
aryl halide. The salient features of this reaction include the readily
available starting materials, general substrate scope, high enantioselectivity,
ease of scale-up, mild reaction conditions, and versatile transformations.