Titanium isopropoxide-mediated cis-selective synthesis of 3,4-substituted butyrolactones from CO2?
Chemical Communications Pub Date: 2022-02-14 DOI: 10.1039/D2CC00446A
Abstract
We report a Ti(OiPr)4-mediated multicomponent reaction, which produces 3,4-substituted cis-δ-lactones from alkyl magnesium chloride, benzaldehyde and CO2. The key intermediate, titanacyclopropane, is formed in situ from Ti(OiPr)4 and a Grignard reagent, which enables 1,2-dinucleophilic reactivity that is used to insert carbon dioxide and an aldehyde. An alternative reaction route is also described where a primary alkene is used to create the titanacyclopropane. A computational analysis of the elementary steps shows that the carbon dioxide and the aldehyde insertion proceeds through an inner-sphere mechanism. A variety of cis-butyrolactones can be synthesized with up to 7?:?1 diastereoselectivity and 77% yield.
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Journal Name：Chemical Communications
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CAS no.: 89640-58-4
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