Science of Synthesis

Hata, S.; Sibi, M. P., Science of Synthesis: Stereoselective Synthesis, (2011) 1, 873.

General Introduction

Carbon—carbon double and triple bonds can undergo radical additions, effectively generating an intermediate radical, which can be further utilized in other bond-forming processes.[‌1‌–‌5‌] The introduction of stereochemistry during these radical reactions has been investigated intensively since the 1980s by synthetic chemists. These reactions are complementary to ionic reactions and often have features that are unique. Earlier investigations involved reactions that were either reagent or substrate controlled.[‌6‌–‌8‌] The nature of these reactions means that stoichiometric amounts of the chiral source are required, either in the reactant or in the substrate. In the past decade, enantioselective radical reactions have emerged that employ catalytic amounts of the chiral source. There are several recent accounts which provide detailed information on various aspects of stereoselective radical reactions.[‌9‌–‌11‌] This chapter provides an overview of the field and includes at least one representative example for each type of stereoselective process involved.

References