(3 + 2) Cycloaddition of 1,3-Dipoles

The cycloaddition of a 1,3-dipole to an alkene for the synthesis of five-membered rings is a classic reaction in organic chemistry. The 1,3-dipolar cycloaddition (1,3-DC) reactions are used for the preparation of molecules of fundamental importance for both academia and industry. In particular, the catalytic asymmetric version of 1,3-DC to produce biologically important and synthetically useful chiral heterocycles has met with tremendous progresses in the past decades. In this chapter, we present a comprehensive introduction of catalytic asymmetric 1,3-DC reactions. A series of widely used 1,3-dipoles, diverse dipolarophiles and different catalytic systems including transition-metal catalysis, Lewis acid catalysis as well as organocatalysis will be discussed in detail.