Catalytic Asymmetric Synthesis of Bicycloprolines by a 1,3-Dipolar Cycloaddition/Intramolecular Alkylation Strategy

The diastereoselective one-pot synthesis of hexahydrocyclopenta­[<i>b</i>]­pyrrole derivatives (bicycloprolines) has been achieved by base-mediated reactions of (<i>E</i>)-<i>tert</i>-butyl 6-bromo-2-hexenoate with α-imino esters. The catalytic asymmetric version of this process has been efficiently achieved using the Cu^I/(<i>R</i>)-DTBM-Segphos complex as a catalyst following a two-step 1,3-dipolar cycloaddition/intramolecular alkylation sequence