Chloromethyl-lithium generated in situ, reacts at –78 °C with ketones (5) to afford, after lithiation with lithium naphthalenide, β-oxidoalkyl-lithium compounds (1), which on reaction with electrophiles (deuterium oxide, dimethyl disulphide, carbon dioxide, cyclohexanone, and allyl bromide) yield bifunctionalized compounds (6).
J. Barluenga, J. L. Fernández-Simón, J. M. Concellón and M. Yus, J. Chem. Soc., Chem. Commun., 1987, 915 DOI: 10.1039/C39870000915
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