Abstract
The reactions of nitrones with terminal alkynes, catalysed by a range of HETPHOX ligands afforded β-lactams in moderate to good conversions with ees up to 55%. High levels of diastereoselectivity, dependent on the alkyne, were obtained. For example, the reaction is highly cis-diastereoselective with phenylacetylene (>9:1), while an unexpected reversal of diastereoselectivity is observed with the 3,5-trifluoromethyl phenylacetylene, which is highly trans selective (1:9) with an ee of 53%. The reaction scope with differently substituted nitrones and phenylacetylenes was also studied.
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