Stereoselective Mannich Reaction of N‐(tert‐Butylsulfinyl)imines with 3‐Fluorooxindoles and Fluoroacetamides

Abstract

AbstractA diastereoselective Mannich reaction has been developed for the construction of stereogenic C−F units by the reaction of α‐fluoro‐substituted amides, including highly activated 3‐fluoro‐oxindoles, and simple linear fluoroacetamides with N‐tert‐butylsulfinylimines. This method provides a concise route to a variety of structurally diverse α‐fluoro‐β‐amino amides containing stereogenic fluorinated carbon centers. This protocol has the benefit of using readily accessible starting materials and is operationally simple. The Mannich reactions of cyclic and linear α‐fluoro‐substituted amides resulted in different stereochemical outcomes, suggesting that these substrates reacted via closed and open transition states, respectively.magnified image