Facial stereocontrol is possible in Michael additions of nucleophiles (Nu) to alkylidene bis(sulfoxides), which proceed via nonchelated (A) or chelated (B) intermediates depending on the addition of an appropriate Lewis acid (LA). This intriguing reactivity could be applied to the first total synthesis of the succinate-based natural product, (+)-erythro-roccellic acid.
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Brebion et al. (2003) studied this question.
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