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Stereocontrolled Synthesis of Triols Containing Four Asymmetric Centers: Application of C,O‑Chelated Germyl Enolates to a Diastereoselective Aldol Reaction

Posted on 2018-06-22 - 20:47
The treatment of α,β-unsaturated ketones with divalent germanium salts cleanly generated C,O-chelated germyl enolates. The aldol reactions of the chelated enolates with the aldehydes achieved a high diastereoselectivity in the construction of the five-membered aldol adducts. Furthermore, the subsequent transformation of the Ge–C bond in the aldol adduct enabled the stereocontrolled synthesis of triols bearing four asymmetric centers.

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