Single and double reductive cleavage of CO bonds of aromatic dimethyl acetals and ketals: Generation of benzylic mono- and dicarbanions
1994; Elsevier BV; Volume: 35; Issue: 36 Linguagem: Inglês
10.1016/s0040-4039(00)73488-5
ISSN1873-3581
AutoresUgo Azzena, Giovanni Melloni, Luisa Pisano, Barbara Sechi,
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoThe reductive cleavage of aromatic dimethyl acetals and ketals, 1, with Li metal in THF at low temperature allows the generation of stable α-alkoxy-α-arylsubstituted carbanions, avoiding the Wittig rearrangement. Reaction of these carbanions with various electrophiles afforded the expected products 2. Further in situ reaction of compounds 2 afforded the products of reductive electrophilic disubstitution, 3.
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