Catalysis

Enantioselective Hydroalkenylation and Hydroalkynylation of Alkenes Enabled by a Transient Directing Group

Authors

  • Amit Simlandy The Scripps Research Institute - United States ,
  • Johny Nguyen The Scripps Research Institute - United States ,
  • Lucas Oxtoby The Scripps Research Institute - United States ,
  • Quynh Wong The Scripps Research Institute - United States ,
  • Jason Chen The Scripps Research Institute - United States ,
  • Keary Engle The Scripps Research Institute - United States

Abstract

The catalytic enantioselective synthesis of α-chiral alkenes and alkynes represents a powerful strategy for rapid generation of molecular complexity. Herein, we report a transient directing group facilitated site-selective palladium-catalyzed reductive Heck-type hydroalkenylation and hydroalkynylation of alkenylaldehyes using alkenyl and alkynyl bromides, respectively, allowing for construction of a stereocenters at the δ position with respect to the aldehyde.

Content

Thumbnail image of Manuscript.pdf

Supplementary material

Thumbnail image of Supporting Info.pdf
Supporting Info
Experimental procedures, characterization data for new compounds, copies of NMR spectra and SFC chromatograms, X-ray crystallographic data
Thumbnail image of 3ak.cif
3ak_CIF
Crystallographic information file for compound 3ak