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Trialkylborane as an Initiator and Terminator of Free Radical Reactions. Facile Routes to Boron Enolates via α-Carbonyl Radicals and Aldol Reaction of Boron Enolates

1991; Oxford University Press; Volume: 64; Issue: 2 Linguagem: Inglês

10.1246/bcsj.64.403

1348-0634

Kyoko Nozaki, Koichiro Oshima, Kiitirô Utimoto,

Radical Photochemical Reactions

Abstract A variety of trialkylborane-induced reactions were examined for the preparation of the α-carbonyl radicals: (1) addition of alkyl radical to methyl vinyl ketone, (2) reduction of α-halo ketone, and (3) intramolecular radical addition to α,β-unsaturated carbonyl moiety. Trialkylborane reacted with α-carbonyl radicals to give boron enolates. The resulting boron enolates were efficiently trapped by carbonyl compounds to give β-hydroxy ketones in good yields.