Abstract
A procedure for producing 1,4-dianion equivalents consists of reductive lithiation, induced by 4,4.-di- tert-butylbiphenylide, of functionalized phenyl sulfides. Nucleophilic addition of 4-lithio-2-(trimethylsilylmethyl)but-1-ene 1 and 2-(3-lithiopropyl)-2-trimethylsilyl-1,3-dithiane 2 thus prepared to N-phenethyl- cis-norbor-5-en-2,3-dicarboximide 9 afforded the corresponding α-hydroxy lactams in good yields. Besides, access to C-10b substituted α,β-unsaturated pyrroloisoquinolinones 3 was efficiently achieved via a tandem organolithium nucleophilic addition — N-acyliminium ion cyclization sequence and subsequent retro Diels-Alder reaction. The methodology can be extended to functionalized organolithiums, but the N-acyliminium cyclization fails if the allylsilane moiety is present.
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