Enantioselective Michael Spirocyclization of Palladium Enolates
Christian Santiago Strong, Peng-Jui Chen, Sanzhar Bissenali, William A. Goddard III, Brian M. Stoltz
TL;DR
A new chemical reaction is developed to create complex 3D carbon structures with high precision.
Contribution
A novel enantioselective Michael spirocyclization of palladium enolates is introduced.
Findings
The reaction forms adjacent all-carbon quaternary and tertiary stereocenters efficiently.
Quantum mechanics calculations reveal the mechanism and stereoselectivity origins.
Abstract
We report an enantioselective and diastereoselective Michael spirocyclization reaction of tetrasubstituted palladium enolates. This allows for the formation of adjacent all-carbon quaternary and tertiary stereocenters in good yield, dr, and ee. Various subsequent cyclization reactions enable access to a diverse range of tricyclic scaffolds. The mechanism of this transformation and the origins of stereoselectivity are investigated via quantum mechanics calculations.
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Taxonomy
TopicsAsymmetric Synthesis and Catalysis · Catalytic C–H Functionalization Methods · Chemical synthesis and alkaloids