Synthesis of a chiral quaternary carbon center bearing a fluorine atom: enantio- and diastereoselective guanidine-catalyzed addition of fluorocarbon nucleophiles.
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.
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.
Zhiyong
Z
Jiang
Yuanhang
Y
Pan
Yujun
Y
Zhao
Ting
T
Ma
Richmond
R
Lee
Yuanyong
Y
Yang
Kuo-Wei
KW
Huang
Ming Wah
MW
Wong
Choon-Hong
CH
Tan