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2005
Organo-tin compounds
S 4800
Novel Kumada Coupling Reaction to Access Cyclic (2-Azaallyl)stannanes. Cycloof Cyclic Nonstabilized 2-Azaallyllithium Species Derived from Cyclic
04- 184 additions
(2-Azaallyl)stannanes. — Stannanes (III) and (XXI) are prepared by treatment of thioether (I) with primary alkyl, aryl, and allylic Grignard compounds or alkylzinc bromide
(IId) in the presence of Ni- or Pd-catalysts. Stannanes (III) are found to be viable precursors to reactive azaallyllithium species or azomethine ylides, which undergo [3 + 2]
cycloaddition reactions with dipolarophiles to give the cycloadducts with high diastereoselectivity. In addition, cross-coupling of thiol (XXII) with Grignard reagents
under the present conditions is an alternative to current methods for the generation of
cyclic imines. — (MANS, D. M.; PEARSON*, W. H.; J. Org. Chem. 69 (2004) 19,
6419-6426; Dep. Chem., Univ. Mich., Ann Arbor, MI 48109, USA; Eng.) — Klein
2005
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