Bruce Lockett-Walters, Cristina Trujillo, Brendan Twamley and Stephen Connon
Chem. Commun., 2019,55, 11283-11286
DOI:
10.1039/C9CC05064G,
Communication
A combined experimental and computational investigation has revealed that the base-catalysed Tamura cycloaddition between homophthalic anhydride and activated alkenes/alkynes – a reaction previously thought of as a Diels–Alder type process – proceeds via a stepwise mechanism involving conjugate addition and ring closure; which allowed the first catalytic asymmetric α-substitution reactions to be demonstrated with up to >99% ee.