The alkylation of the (±)-spiro-γ-lactones 1 and 5a occurs with high diastereofacial selectivity. Geometry-optimized ab initio 4-31G calculations on enol 7 suggest that electrophilic attack occurs at an angle of about 80° to the plane of the enolate, together with a displacement of the trajectory away from the oxygen linked to lithium.
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Pellissier et al. (1997) studied this question.
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