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.
Highlights
Aleksi Sahari, a Cuong Dat Do, b Jere K
We report a Ti(OiPr)4-mediated multicomponent reaction, which produces 3,4-substituted cis-d-lactones from alkyl magnesium chloride, benzaldehyde and CO2
A computational analysis of the elementary steps shows that the carbon dioxide and the aldehyde insertion proceeds through an inner-sphere mechanism
Summary
Aleksi Sahari, a Cuong Dat Do, b Jere K. 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.
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