Cascade Grignard Addition: Propargyl Claisen Rearrangement for the Stereoselective Synthesis of α-Allene Quaternary Centers in Cyclohexanones
Year: 2025
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide We report a new method for the enantio- and diastereoselective synthesis of α-allene quaternary centers in fully substituted cyclohexanones at the α-positions. This reaction involves asymmetric 1,2-carbonyl addition to 2- O -propargyl enones using a mixture of Grignard reagents and the PMP-H8-BINOL ligand. The resulting magnesium alkoxide chelate intermediate then activated the propargyl vinyl ether moiety, thereby triggering a cascade propargyl Claisen rearrangement in a diastereoselective manner. The synthetic applications of this method in the context of complex molecules are also demonstrated.
Source: Organic Letters
Authors: Estefania Armendariz-Gonzalez, Adi Saputra, Edward W. Mureka, Cale M. Locicero, Gabrielle L. Womble, Gloria Tan, Abigail A. Watson, Frank R. Fronczek, Rendy Kartika
Institution: Louisiana State University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
OpenAlex ID: W4411415299