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Radical cyclization of α-bromo aluminum acetals onto alkenes and alkynes (radic[Al] process): a simple access to γ-lactols and 4-methylene-γ-lactols



Radical cyclization of α-bromo aluminum acetals onto alkenes and alkynes (radic[Al] process): a simple access to γ-lactols and 4-methylene-γ-lactols



Chemistry 17(20): 5613-5627



An efficient preparation of γ-lactols and methylene-γ-lactols is described. Highly acid-sensitive lactols are prepared in a concise manner by using a radical cyclization of aluminum acetals. The precursors for the radical reactions are readily prepared from allyl or propargyl alcohols and α-bromo acids. Functionalization of the resulting γ-lactols and methylene-γ-lactols can be achieved following isolation, leading to synthetically useful building blocks, such as 1,4-diols, 1,4-dienes, γ-lactones, and polysubstituted tetrahydrofurans.

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Accession: 055345752

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PMID: 21472805

DOI: 10.1002/chem.201100049


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