Conditions for a Rh(I)-catalyzed [2 + 2 + 1] cycloaddition reaction with methyl substituted allenes and alkynes

Sarah M Wells; Kay M Brummond

doi:10.1016/j.tetlet.2015.01.075

Conditions for a Rh(I)-catalyzed [2 + 2 + 1] cycloaddition reaction with methyl substituted allenes and alkynes

Tetrahedron Lett. 2015 Jun 3;56(23):3546-3549. doi: 10.1016/j.tetlet.2015.01.075.

Authors

Sarah M Wells¹, Kay M Brummond¹

Affiliation

¹ Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.

Abstract

The direct installation of the C4 and C10 methyl groups present in the 6,12-guaianolide framework using a Rh(I)-catalyzed cyclocarbonylation reaction of methyl subsituted allenes and alkynes is described. High yields of bicyclo[5.3.0]decanes are afforded when low reaction concentrations involving syringe pump addition of the allene-yne to the catalyst are used.

Keywords: Allene-yne; Bicyclo[5.3.0]decadienone; Guaianolide; High Dilution; Pauson-Khand; Solid-supported Scavenger.

Grants and funding

R01 GM054161/GM/NIGMS NIH HHS/United States