Titanium isopropoxide-mediated cis-selective synthesis of 3,4-substituted butyrolactones from CO2
Permanent lenke
https://hdl.handle.net/10037/24638Dato
2022-02-14Type
Journal articleTidsskriftartikkel
Peer reviewed
Forfatter
Sahari, Aleksi; Do, Cuong Dat; Mannisto, Jere K.; Antico, Emanuele; Amaratunga, Angelo; Hopmann, Kathrin Helen; Repo, TimoSammendrag
We report a Ti(OiPr)4-mediated multicomponent reaction, which
produces 3,4-substituted cis-d-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 cisbutyrolactones can be synthesized with up to 7 : 1 diastereoselectivity and 77% yield.
Forlag
Royal Society of ChemistrySitering
Sahari A, Do CD, Mannisto JK, Antico, Amaratunga, Hopmann KH, Repo T. Titanium isopropoxide-mediated cis-selective synthesis of 3,4-substituted butyrolactones from CO2. Chemical Communications. 2022;58:3027-3030Metadata
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