4.4 Article

Diastereoselective sulfur ylide rearrangements from gold catalyzed oxidation of ynamides

Journal

TETRAHEDRON
Volume 78, Issue -, Pages -

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2020.131757

Keywords

Sulfur ylide; Rearrangement; Gold carbenoid; Oxidation; Ynamide

Funding

  1. University of Birmingham
  2. EPSRC [EP/K502984/1]
  3. Centre for Chemical and Materials analysis in the School of Chemistry

Ask authors/readers for more resources

This study demonstrates high diastereoselectivity in the synthesis of allyl sulfonium ylides through a gold-catalyzed multicomponent route. Modifying the substrate structure, N-phenyl methanesulfonamide derived ynamides are found to be the most effective precursors.
The [2,3]-sigmatropic rearrangement of sulfonium ylides bearing substituted allyl groups creates two contiguous stereocentres. Low diastereoselectivity is typically observed from commonly used alpha-diazocarboxylic ester precursors. High diastereoselectivity was previously revealed in a gold-catalyzed multicomponent route into allyl sulfonium ylides by reaction of ynamide, oxidant and allyl sulfides. The effect of substrate modifications on the diastereoselectivity have been studied, with N-phenyl methanesulfonamide derived ynamides proving the most effective. This report includes an enhanced experimental procedure, and a demonstration that the gold-catalyzed process remains highly effective at -78 degrees C. (C) 2020 Elsevier Ltd. All rights reserved.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.4
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

No Data Available
No Data Available