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3.4.7.5.1 Variation 1: Substitution Reactions

DOI: 10.1055/sos-SD-003-00274

Heaney, H.; Christie, S.Science of Synthesis, (20043617.

The displacement of primary halides to produce new CC bonds using Gilman cuprates is not at all common. Part of the reason is the ease of facilitating this reaction with only catalytic amounts of copper, therefore rendering the formation of the stoichiometric cuprate an extraneous step. However, when applied to other displacement reactions, cuprates often show increased or different activity than other copper species. Perhaps most useful is the opening of epoxides to afford substituted products. In general, these reactions proceed well with alkylcuprates, producing the expected products in good yield with control over both regio- and stereoselectivity. For example, as shown in Scheme 481, simple cuprates can be added to chiral epoxides to produce β-hydroxy esters.[‌1613‌] In appropriately substituted cases the alkoxide formed can react with a pendant ester to produce the corresponding lactone.[‌1614‌] Substituted cuprates can also be employed. An example illustrated shows an acetal-substituted alkylcuprate reacting to form the alcohol product in excellent yield.[‌187‌]

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