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Radical Additions in Aqueous Medium: Direct Synthesis of 5‐Allyl‐Substituted γ‐Lactones from Allylic Bromides/Zinc and Methyl γ‐Oxocarboxylates
Author(s) -
Kunz Thomas,
Reißig HansUlrich
Publication year - 1989
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198919890240
Subject(s) - allylic rearrangement , chemistry , zinc , aqueous medium , yield (engineering) , lewis acids and bases , organic chemistry , aqueous solution , medicinal chemistry , catalysis , materials science , metallurgy
Following a procedure published by Luche, 5‐allyl‐substituted γ‐lactones 2a–2d are prepared in good yield from methyl γ‐oxocarboxylates 1a–1c and allyl bromides/zinc dust in aqueous medium. The diastereoselectivity of this allylation reaction is compared to that of Lewis acid promoted additions of allyltrimethylsilane to chiral aldehydes.