Highly Regio- and Diastereoselective Addition of Organolithium Reagents to Chiral Fluoroalkyl alpha,beta-Unsaturated N-tert-Butanesulfinyl Ketimines: A General and Efficient Access to alpha-Tertiary Fluoroalkyl Allylic Amines and alpha-Fluoroalkyl alpha-Amino Acids

Highly regio-and diastereoselective 1,2-addition of organolithium reagents to chiral fluoroalkyl alpha,beta-unsaturated N-tert-butanesulfinyl ketimines was developed, providing a general and efficient method for the asymmetric synthesis of structurally diverse alpha-tertiary fluoroalkyl allylic amines in high yields and with excellent diastereoselectivities (dr up to >99: 1). The synthetic application of the method was demonstrated by the rapid and convenient preparation of challenging alpha-fluoroalkyl alpha-amino acids with alpha-tetrasubstituted carbon.