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Radical addition to 2‐cyclohexyl‐5‐methylidene‐6‐methyl‐1,3‐dioxan‐4‐one (2) affords stereoselectively 5,6‐trans‐products trans‐3. The size of the radical has no influence on the selectivity. These trans‐acetals are converted into threo‐3‐hydroxy‐butanoates 4. Methyl 2‐methylidene‐3‐[(tert‐butyl)diphenylsilyloxy]butanoate (5), treated under the same conditions, leads mainly to the erythro‐isomer of 4 after deprotection. An influence of the steric bulkyness of the radical is observed. The stereochemical course of the reactions is discussed.
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Bulliard et al. (1991) studied this question.
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