The tin(II) enolates of cyclic ketones were found to react with β-nitrostyrene to afford the corresponding 4-nitroketones with unprecedented anti-selectivity. In the case of the reaction of the tin(II) enolate of cyclohexanone with β-nitrostyrene, the anti-adduct was yielded in >93:7 diastereomeric excess.
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Stevens et al. (1985) studied this question.
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