The scope and limitations of 1,3-dipolar cycloaddition reactions between nitrile oxides and chiral α,β-unsaturated-γ-sultams 2a and 2b have been investigated. Only very marginal diastereoselectivity was observed for the reaction. In contrast, using double asymmetric induction strategy, the cycloaddition products from 2a and chiral nitrones were obtained in better diastereomeric ratios (up to 7.1:1).
Keywords: dipolar, cycloaddition, chiral sultams, nitrile oxides, nitrones
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