Organocatalyzed Asymmetric Allylic Alkylation Enables Synthesis of Chiral γ-Lactones Bearing Vicinal Tertiary and Quaternary Stereocenters

The synthesis of enantioenriched alpha-aryl-alpha'-allyl-gamma- butyrolactones bearing vicinal tertiary and quaternary stereocenters through organocatalyzed asymmetric allylic alkylation is reported. The process demonstrated that weakly stabilized enolates derived from alpha- aryl-gamma-butyrolactones can undergo regio-, diastereo-, and enantiose-lective allylation using the proper activation of Morita-Baylis- Hillman (MBH) carbonates.

Automated summary

In this study, the synthesis of enantioenriched alpha-aryl-alpha'-allyl-gamma-butyrolactones bearing vicinal tertiary and quaternary stereocenters through organocatalyzed asymmetric allylic alkylation was reported.