Efficient Stereo-Selective Fluorination on Vitamin D3 Side-Chain Using Electrophilic Fluorination

Abstract

Our research regarding side-chain fluorinated vitamin D₃ analogues has explored a series of efficient fluorination methods. In this study, a new electrophilic stereo-selective fluorination methodology at C24 and C22 positions of the vitamin D₃ side-chain was developed using N-fluorobenzenesulfonimide (NFSI) and CD-ring imides with an Evans chiral auxiliary (26,27,30).

Keywords: Evans chiral auxiliary; N-fluorobenzenesulfonimide (NFSI); electrophilic fluorination; side-chain; side-chain fluorinated vitamin D3.