Abstract
Alkylation of α,β-unsaturated imines is achieved through C-H bond activation. The N-benzyl imines were alkylated with various terminal alkenes (one example with a terminal alkyne) and very high Z/E ratios were obtained (>95:5 Z/E) for the imine product. Hydrolysis to the aldehyde often resulted in isomerization of the olefin. A mild hydrolysis protocol using activity III neutral alumina was developed to provide the aldehyde with a high integrity of retention of stereochemistry.
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