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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
Author(s) -
Boussonnière Anne,
Bénéteau Romain,
Zimmermann Nicolas,
Lebreton Jacques,
Dénès Fabrice
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201100049
Subject(s) - methylene , propargyl , chemistry , organic chemistry , acetal , radical cyclization , catalysis
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.