Scope and limitations in the use of α-silyl and α-stannyl sulfones as latent α-sulfonyl anions
Three methods for the regeneration of α-sulfonyl anions from α-silyl sulfones and α-stannyl sulfones are investigated. These methods include: (1) treatment of α-silyl sulfones with electrophiles (aldehydes and acid halides) in the presence of fluoride ion; (2) reaction of α-silyl sulfones with n-butyllithium which produces an α-silyl anion via a migration of the -SiMe3 group from the α-position to the ortho-position of the phenyl sulfones; and (3) direct transmetalation of α-stannyl sulfone by treatment with n-butyllithium. The addition of cerium [III] chloride is shown to substantially decrease enolization problems associated with addition of α-sulfonyl anions to carbonyl compounds bearing enolizable protons.
Lamothe,Anderson,Fuchs
p. 1675 - 1693
(2007/10/02)
Intramolecular Acylation of an α-Sulfonyl Anion Generated via Halogen-metal Exchange of an α-Halosulfone Bearing an Unsymmetrical Anhydride
α-Halosulfones are useful for the in situ preparation of α-sulfonyl anions in the presence of acylating agents bearing enolizable protons.Inter- and intramolecular acylations can be effected by halogen-metal exchange at low temperature.
Anderson, M. B.,Lamothe, M.,Fuchs, P. L.
p. 4457 - 4460
(2007/10/02)
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