Synthesis of a Chiral Quaternary Carbon Center Bearing a Fluorine Atom:

Enantio‐ and Diastereoselective Guanidine‐Catalyzed Addition of Fluorocarbon Nucleophiles

Zhiyong Jiang Dr., Yuanhang Pan, Yujun Zhao, Ting Ma, Richmond Lee, Yuanyong Yang, Kuo‐Wei Huang Prof., Ming Wah Wong Prof. and Choon‐Hong Tan Prof.

Angewandte Chemie International Edition, 2009, 48, 3627 –3631. (Hot paper)

Abstract: The perfect combination: The title reaction provides adducts having quaternary carbon centers bearing a fluorine atom with high ee and d.r. values (see scheme). The mechanism and origin of stereoselectivity were elucidated by DFT calculations. The bifunctional mode of the guanidine catalysis was demonstrated in the transition states resulting from the DFT results.

Paper download: https://doi.org/10.1002/anie.200900964